Heterobicyclic compounds used as fungicides

ABSTRACT

Bicyclic compounds of the formula I  
                 
in which 
     A 1  or A 5  is C and the other of the two variables A 1 , A 5  is N, C or C—R 3 ;    A 2 , A 3 , A 4  independently of one another are N or C—R 3a , 
       where one of the variables A 2 , A 3  or A 4  may also be S or a group N—R 4  if A 1  and A 5  are both C,    
       and where A 4  is not N or C—R 3a  if A 1  is N, A 3  is C—R 3a  and A 5  is C, and where 
       A 1  is attached to A 2  and A 3  to A 4  or    A 2  is attached to A 3  and A 4  to A 5  or    A 1  is attached to A 5  and A 2  to A 3  or    A 1  is attached to A 5  and A 3  to A 4  or    A 1  is attached to A 2  and A 4  to A 5  by double bonds; n is 0, 1, 2, 3, 4 or 5;    
       R a  is halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkyl, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy or C(O)R 5 ;    R 1  is halogen, cyano, C 1 -C 10 -alkyl, where a carbon atom of the C 1 -C 10 -alkyl radical may be replaced by a silicium atom, C 1 -C 6 -haloalkyl, C 2 -C 10 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl, where the cycloalkyl moiety of the two last-mentioned groups may be unsubstituted or contain 1, 2, 3, 4, 5, or 6 radicals selected from the group consisting of C 1 -C 4 -alkylidene, C 1 -C 4 -alkyl, halogen, C 1 -C 4 -haloalkyl and hydroxy and the alkyl moiety of C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl may be unsubstituted or contain 1, 2, 3, or 4 radicals selected from the group consisting of halogen, C 1 -C 4 -haloalkyl and hydroxy, C 5 -C 8 -cycloalkenyl which may be unsubstituted or contain 1, 2, 3 or 4 radicals selected from the group consisting of C 1 -C 4 -alkyl, halogen, C 1 -C 4 -haloalkyl and hydroxy, OR 6 , SR 6 , NR 7 R 8 , a radical of the formula —C(R 11 )(R 12 )C(═NOR 13 )(R 14 ) or a radical of the formula —C(═NOR 15 )C(═NOR 16 )(R 17 );    R 2  is halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 5 -C 8 -cycloalkenyl, OR 6 , SR 6  or NR 7 R 8 ; and the agriculturally acceptable salts of the compounds I, crop protection compositions comprising at least one compound of the formula I and/or an agriculturally acceptable salt of I and at least one solid or liquid carrier and a method for controlling phytopathogenic harmful fungi are described.

The present invention relates to novel bicyclic compounds and to theiruse for controlling harmful fungi, and to crop protection compositionscomprising such compounds as active ingredients.

EP-A 71792, U.S. Pat. No. 5,994,360, EP-A 550113 and WO 02/48151describe fungicidally active pyrazolo[1,5-a]pyrimidines andtriazolo[1,5-a]pyrimidines which carry a substituted or unsubstitutedphenyl group in the 5-position of the pyrimidine ring.Imidazolo[1,2-a]pyrimidines having fungicidal action are known from WO03/022850.

EP-A 770615 describes a process for preparing 5-arylazolopyrimidineswhich have a chlorine or bromine atom in the 4- and in the 6-position ofthe pyrimidine ring.

The fungicidal action of the azolopyrimidines known from the prior artis sometimes not satisfactory, or the compounds have unwantedproperties, such as low crop plant safety.

It is an object of the present invention to provide novel compoundshaving improved fungicidal activity and/or better crop plant safety.This object is achieved by bicyclic compounds of the formula I

in which

-   A₁ or A₅ is C and the other of the two variables A₁, A₅ is N, C or    C—R³;-   A₂, A₃, A₄ independently of one another are N or C—R^(3a),

where one of the variables A₂, A₃ or A₄ may also be S or a group N—R⁴ if

A₁ and A₅ are both C, and where

A₁ is attached to A₂ and A₃ to A₄ or

A₂ is attached to A₃ and A₄ to A₅ or

A₁ is attached to A₅ and A₂ to A₃ or

A₁ is attached to A₅ and A₃ to A₄ or

A₁ is attached to A₂ and A₄ to A₅ by double bonds;

-   n is 0, 1, 2, 3, 4 or 5;-   R^(a) is halogen, cyano, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkyl,    C₁-C₆-haloalkoxy, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy or C(O)R⁵;-   R¹ is halogen, cyano, C₁-C₁₀-alkyl, where a carbon atom of the    C₁-C₁₀-alkyl radical may be replaced by a silicium atom,    C₁-C₆-haloalkyl, C₂-C₁₀-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,    C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, where the cycloalkyl    moiety of the two last-mentioned groups may be unsubstituted or    contain 1, 2, 3, 4, 5, or 6 radicals selected from the group    consisting of C₁-C₄-alkylidene, C₁-C₄-alkyl, halogen,    C₁-C₄-haloalkyl and hydroxy and the alkyl moiety of    C₃-C₈-cycloalkyl-C₁-C₄-alkyl may be unsubstituted or contain 1, 2,    3, or 4 radicals selected from the group consisting of halogen,    C₁-C₄-haloalkyl and hydroxy, C₅-C₈-cycloalkenyl which may be    unsubstituted or contain 1, 2, 3 or 4 radicals selected from the    group consisting of C₁-C₄-alkyl, halogen, C₁-C₄-haloalkyl and    hydroxy, OR⁶, SR⁶, NR⁷R⁸, a radical of the formula    —C(R¹¹)(R¹²)C(═NOR¹³)(R¹⁴) or a radical of the formula    —C(═NOR¹⁵)C(═NOR¹⁶)(R¹⁷);-   R² is halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,    C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl,    C₅-C₈-cycloalkenyl, OR⁶, SR⁶ or NR⁷R⁸;-   R³, R^(3a) independently of one another are hydrogen, CN, halogen,    C₁-C₆-alkyl or C₂-C₆-alkenyl;-   R⁴ is hydrogen, C₁-C₆-alkyl or C₂-C₆-alkenyl;-   R⁵ is hydrogen, OH, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkyl,    C₁-C₆-haloalkoxy, C₂-C₆-alkenyl, C₁-C₆-alkylamino or    di-C₁-C₆-alkylamino, piperidin-1-yl, pyrrolidin-1-yl or    morpholin-4-yl;-   R⁶ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl or COR⁹;-   R⁷, R⁸ independently of one another are hydrogen, C₁-C₁₀-alkyl,    C₂-C₁₀-alkenyl, C₄-C₁₀-alkadienyl, C₂-C₁₀-alkynyl, C₃-C₈-cycloalkyl,    C₅-C₈-cycloalkenyl, C₅-C₁₀-bicycloalkyl, phenyl, naphthyl,    -   a 5- or 6-membered saturated or partially unsaturated        heterocycle which may have 1, 2 or 3 heteroatoms selected from        the group consisting of N, O and S as ring members or    -   a 5- or 6-membered aromatic heterocycle which may have 1, 2 or 3        heteroatoms selected from the group consisting of N, O and S as        ring members,    -   where the radicals mentioned as R⁷, R⁸ may be partially or fully        halogenated and/or may have 1, 2 or 3 radicals R^(b) where R^(b)        is selected from the group consisting of cyano, nitro, OH,        C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy,        C₁-C₆-alkylthio, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkynyl,        C₂-C₆-alkynyloxy, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino,        piperidin-1-yl, pyrrolidin-1-yl or morpholin-4-yl;-   R⁷ and R⁸ together with the nitrogen atom to which they are attached    may also form a 5-, 6- or 7-membered saturated or unsaturated    heterocycle which may have 1, 2, 3 or 4 further heteroatoms selected    from the gorup consisting of O, S, N and NR¹⁰ as ring members, which    may be partially or fully halogenated and which may have 1, 2 or 3    radicals R^(b);-   R⁹, R¹⁰ independently of one another are hydrogen or C₁-C₆-alkyl;-   R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷ are, independently of one another,    hydrogen or C₁-C₆-alkyl;    subject to the proviso that A₁ does not represent N when A₅ is C and    A₂, A₃ and A₄ concurrently have the following meanings: A₂ is N or    C—R^(3a), A₃ is C—R^(3a) and A₄ is N or C—R^(3a);    and the agriculturally acceptable salts of compounds I.

Accordingly, the present invention provides the bicyclic compounds ofthe formula I and their agriculturally acceptable salts, except forcompounds of the formula I in which R¹ and R² are both OH or bothhalogen, if A₁ is N and A₅ is C and the variables A₂, A₃ and A₄independently of one another are N or C—R^(3a).

Furthermore, the present invention provides the use of the bicycliccompounds of the formula I and their agriculturally acceptable salts forcontrolling phytopathogenic fungi (=harmful fungi), and a method forcontrolling phytopathogenic harmful fungi which comprises treating thefungi or the materials, plants, the soil or seeds to be protectedagainst fungal attack with an effective amount of a compound of theformula I and/or an agriculturally acceptable salt of I.

The present invention provides compositions for controlling harmfulfungi, which compositions comprise at least one compound of the formulaI and/or an agriculturally acceptable salt thereof and at least oneliquid or solid carrier.

Depending on the substitution pattern, the compounds of the formula Imay have one or more centers of chirality, in which case they arepresent as mixtures of enantiomers or diastereomers. The inventionprovides both the pure enantiomers or diastereomers and their mixtures.The invention also provides tautomers of compounds of the formula I.

Suitable agriculturally useful salts are especially the salts of thosecations or the acid addition salts of those acids whose cations andanions, respectively, have no adverse effect on the fungicidal action ofthe compounds I. Thus, suitable cations are in particular the ions ofthe alkali metals, preferably sodium and potassium, of the alkalineearth metals, preferably calcium, magnesium and barium, and of thetransition metals, preferably manganese, copper, zinc and iron, and alsothe ammonium ion which, if desired, may carry one to four C₁-C₄-alkylsubstituents and/or one phenyl or benzyl substituent, preferablydiisopropylammonium, tetramethylammonium, tetrabutylammonium,trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions,preferably tri(C₁-C₄-alkyl)sulfonium, and sulfoxonium ions, preferablytri(C₁-C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide,fluoride, hydrogensulfate, sulfate, dihydrogenphosphate,hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate,hexafluorosilicate, hexafluorophosphate, benzoate, and the anions ofC₁-C₄-alkanoic acids, preferably formate, acetate, propionate andbutyrate. They can be formed by reacting I with an acid of thecorresponding anion, preferably of hydrochloric acid, hydrobromic acid,sulfuric acid, phosphoric acid or nitric acid.

In the definitions of the variables given in the formulae above,collective terms are used which are generally representative for thesubstituents in question. The term C_(n)-C_(m) denotes the number ofcarbon atoms possible in each case in the substituent or part of thesubstituent in question:

halogen: fluorine, chlorine, bromine and iodine;

alkyl and all alkyl moieties in alkoxy, alkylthio, alkylamino anddialkylamino: saturated straight-chain or branched hydrocarbon radicalshaving 1 to 4, to 6, to 8 or to 10 carbon atoms, for example C₁-C₆-alkylsuch as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl,2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl,3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl,1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl,3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl,3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl,1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and1-ethyl-2-methylpropyl;

haloalkyl: straight-chain or branched alkyl groups having 1 to 4 or to 6carbon atoms (as mentioned above), where some or all of the hydrogenatoms in these groups may be replaced by halogen atoms as mentionedabove, for example C₁-C₂-haloalkyl such as chloromethyl, bromomethyl,dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl,trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl,chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and1,1,1-trifluoroprop-2-yl;

alkenyl: monounsaturated straight-chain or branched hydrocarbon radicalshaving 2 to 4, to 6, to 8 or to 10 carbon atoms and a double bond in anyposition, for example C₂-C₆-alkenyl such as ethenyl, 1-propenyl,2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl,1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl,2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl,1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl,1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl,1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl,1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl,1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl,1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl,1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl,4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl,3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl,2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl,1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl,4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,1,2-dimethyl-4-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl,1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,2,2-dimethyl-3-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-2-butenyl,2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;

alkadienyl: doubly unsaturated straight-chain or branched hydrocarbonradicals having 4 to 10 carbon atoms and two double bonds in anyposition, for example 1,3-butadienyl, 1-methyl-1,3-butadienyl,2-methyl-1,3-butadienyl, penta-1,3-dien-1-yl, hexa-1,4-dien-1-yl,hexa-1,4-dien-3-yl, hexa-1,4-dien-6-yl, hexa-1,5-dien-1-yl,hexa-1,5-dien-3-yl, hexa-1,5-dien-4-yl, hepta-1,4-dien-1-yl,hepta-1,4-dien-3-yl, hepta-1,4-dien-6-yl, hepta-1,4-dien-7-yl,hepta-1,5-dien-1-yl, hepta-1,5-dien-3-yl, hepta-1,5-dien-4-yl,hepta-1,5-dien-7-yl, hepta-1,6-dien-1-yl, hepta-1,6-dien-3-yl,hepta-1,6-dien-4-yl, hepta-1,6-dien-5-yl, hepta-1,6-dien-2-yl,octa-1,4-dien-1-yl, octa-1,4-dien-2-yl, octa-1,4-dien-3-yl,octa-1,4-dien-6-yl, octa-1,4-dien-7-yl, octa-1,5-dien-1-yl,octa-1,5-dien-3-yl, octa-1,5-dien-4-yl, octa-1,5-dien-7-yl,octa-1,6-dien-1-yl, octa-1,6-dien-3-yl, octa-1,6-dien-4-yl,octa-1,6-dien-5-yl, octa-1,6-dien-2-yl, deca-1,4-dienyl,deca-1,5-dienyl, deca-1,6-dienyl, deca-1,7-dienyl, deca-1,8-dienyl,deca-2,5-dienyl, deca-2,6-dienyl, deca-2,7-dienyl, deca-2,8-dienyl andthe like;

alkynyl: straight-chain or branched hydrocarbon groups having 2 to 4, 2to 6, 2 to 8 or 2 to 10 carbon atoms and a triple bond in any position,for example C₂-C₆-alkynyl such as ethynyl, 1-propynyl, 2-propynyl,1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl,2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl,1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl,1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl,3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl,1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl,2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl,4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl,1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl,3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl,2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;

alkylidene: straight chain or branched hydrocarbon group, having from 1to 4, preferably 1 or 2 carbon atoms, which carries on one carbon atom 2hydrogen atoms less than the parent alkane, e.g. methylene, ethylidene,propylidene, isopropylidene, and butylidene;

cycloalkyl: monocyclic saturated hydrocarbon groups having 3 to 8,preferably to 6, carbon ring members, such as cyclopropyl, cyclobutyl,cyclopentyl and cyclohexyl, which may be unsusbstituted or may carry 1,2, 3, 4, 5, or 6 radicals selected from C₁-C₄-alkylidene, C₁-C₄-alkyl,halogen, C₁-C₄-haloalkyl and hydroxy;

cycloalkenyl: monocyclic monounsaturated hydrocarbon groups having 5 to8, preferably to 6, carbon ring members, such as cyclopenten-1-yl,cyclopenten-3-yl, cyclohexen-1-yl, cyclohexen-3-yl and cyclohexen-4-yl,which may be unsusbstituted or may carry 1, 2, 3 or 4 radicals selectedfrom C₁-C₄-alkyl, halogen, C₁-C₄-haloalkyl and hydroxy;

bicycloalkyl: a bicyclic hydrocarbon radical having 5 to 10 carbonatoms, such as bicyclo[2.2.1]hept-1-yl, bicyclo[2.2.1]hept-2-yl,bicyclo[2.2.1]hept-7-yl, bicyclo[2.2.2]oct-1-yl, bicyclo[2.2.2]oct-2-yl,bicyclo[3.3.0]octyl and bicyclo[4.4.0]decyl;

C₁-C₄-alkoxy: an alkyl group having 1 to 4 carbon atoms which isattached via an oxygen, for example methoxy, ethoxy, n-propoxy,1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or1,1-dimethylethoxy;

C₁-C₆-alkoxy: C₁-C₄-alkoxy as mentioned above and also, for example,pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy,1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy,1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy,3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy,1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy,2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy,1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxyor 1-ethyl-2-methylpropoxy;

C₁-C₄-haloalkoxy: a C₁-C₄-alkoxy radical as mentioned above which ispartially or fully substituted by fluorine, chlorine, bromine and/oriodine, preferably by fluorine, i.e., for example, OCH₂F, OCHF₂, OCF₃,OCH₂Cl, OCHCl₂, OCCl₃, chlorofluoromethoxy, dichlorofluoromethoxy,chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy,2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy,2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy,2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC₂F₅,2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy,2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy,2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy,3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH₂—C₂F₅, OCF₂—C₂F₅,1-(CH₂F)-2-fluoroethoxy, 1-(CH₂Cl)-2-chloroethoxy,1-(CH₂Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxyor nonafluorobutoxy;

C₁-C₆-haloalkoxy: C₁-C₄-haloalkoxy as mentioned above and also, forexample, 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy,5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy,6-bromohexoxy, 6-iodohexoxy or tridecafluorohexoxy;

alkenyloxy: Alkenyl as mentioned above which is attached via an oxygenatom, for example C₂-C₆-alkenyloxy such as vinyloxy, 1-propenyloxy,2-propenyloxy, 1-methylethenyloxy, 1-butenyloxy, 2-butenyloxy,3-butenyloxy, 1-methyl-1-propenyloxy, 2-methyl-1-propenyloxy,1-methyl-2-propenyloxy, 2-methyl-2-propenyloxy, 1-pentenyloxy,2-pentenyloxy, 3-pentenyloxy, 4-pentenyloxy, 1-methyl-1-butenyloxy,2-methyl-1-butenyloxy, 3-methyl-1-butenyloxy, 1-methyl-2-butenyloxy,2-methyl-2-butenyloxy, 3-methyl-2-butenyloxy, 1-methyl-3-butenyloxy,2-methyl-3-butenyloxy, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyloxy,1,2-dimethyl-1-propenyloxy, 1,2-dimethyl-2-propenyloxy,1-ethyl-1-propenyloxy, 1-ethyl-2-propenyloxy, 1-hexenyloxy,2-hexenyloxy, 3-hexenyloxy, 4-hexenyloxy, 5-hexenyloxy,1-methyl-1-pentenyloxy, 2-methyl-1-pentenyloxy, 3-methyl-1-pentenyloxy,4-methyl-1-pentenyloxy, 1-methyl-2-pentenyloxy, 2-methyl-2-pentenyloxy,3-methyl-2-pentenyloxy, 4-methyl-2-pentenyloxy, 1-methyl-3-pentenyloxy,2-methyl-3-pentenyloxy, 3-methyl-3-pentenyloxy, 4-methyl-3-pentenyloxy,1-methyl-4-pentenyloxy, 2-methyl-4-pentenyloxy, 3-methyl-4-pentenyloxy,4-methyl-4-pentenyloxy, 1,1-dimethyl-2-butenyloxy,1,1-dimethyl-3-butenyloxy, 1,2-dimethyl-1-butenyloxy,1,2-dimethyl-2-butenyloxy, 1,2-dimethyl-3-butenyloxy,1,3-dimethyl-1-butenyloxy, 1,3-dimethyl-2-butenyloxy,1,3-dimethyl-3-butenyloxy, 2,2-dimethyl-3-butenyloxy,2,3-dimethyl-1-butenyloxy, 2,3-dimethyl-2-butenyloxy,2,3-dimethyl-3-butenyloxy, 3,3-dimethyl-1-butenyloxy,3,3-dimethyl-2-butenyloxy, 1-ethyl-1-butenyloxy, 1-ethyl-2-butenyloxy,1-ethyl-3-butenyloxy, 2-ethyl-1-butenyloxy, 2-ethyl-2-butenyloxy,2-ethyl-3-butenyloxy, 1,1,2-trimethyl-2-propenyloxy,1-ethyl-1-methyl-2-propenyloxy, 1-ethyl-2-methyl-1-propenyloxy and1-ethyl-2-methyl-2-propenyloxy;

alkynyloxy: Alkynyl as mentioned above which is attached via an oxygenatom, for example C₃-C₆-alkynyloxy such as 2-propynyloxy, 2-butynyloxy,3-butynyloxy, 1-methyl-2-propynyloxy, 2-pentynyloxy, 3-pentynyloxy,4-pentynyloxy, 1-methyl-2-butynyloxy, 1-methyl-3-butynyloxy,2-methyl-3-butynyloxy, 1-ethyl-2-propynyloxy, 2-hexynyloxy,3-hexynyloxy, 4-hexynyloxy, 5-hexynyloxy, 1-methyl-2-pentynyloxy,1-methyl-3-pentynyloxy and the like;

five- or six-membered saturated or partially unsaturated heterocyclewhich contains one, two or three heteroatoms from the group consistingof oxygen, nitrogen and sulfur: for example mono- and bicyclicheterocycles (heterocyclyl) comprising, in addition to carbon ringmembers, one to three nitrogen atoms and/or one oxygen or sulfur atom orone or two oxygen and/or sulfur atoms, for example 2-tetrahydrofuranyl,3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl,2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl,5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl,5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl,2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl,4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl,1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl,1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl,1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl,1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl,2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl,2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl,2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl,3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl,4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl,4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl,4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl,4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl,4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl,4-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl,2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl,2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl,3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl,3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl,4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl,4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl,2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl,3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl,3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl,2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl,2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl,3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl,4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl,1,3,5-hexahydrotriazin-2-yl and 1,2,4-hexahydrotriazin-3-yl;

five- or six-membered aromatic heterocycle which contains one, two orthree heteroatoms from the group consisting of oxygen, nitrogen andsulfur: mono- or bicyclic heteroaryl, for example 5-membered heteroarylwhich is attached via carbon and contains one to three nitrogen atoms orone or two nitrogen atoms and one sulfur or oxygen atom as ring members,such as 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl,3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl,4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl,2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl,5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl,1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl,1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl and1,3,4-triazol-2-yl; 5-membered heteroaryl which is attached via nitrogenand contains one to three nitrogen atoms as ring members, such aspyrrol-1-yl, pyrazol-1-yl, imidazol-1-yl, 1,2,3-triazol-1-yl and1,2,4-triazol-1-yl; 6-membered heteroaryl which contains one to threenitrogen atoms as ring members, such as pyridin-2-yl, pyridin-3-yl,pyridin-4-yl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl,4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl and1,2,4-triazin-3-yl.

A first preferred embodiment of the present invention relates tocompounds of the formula I in which A₁ is attached to A₂ and A₃ to A₄ ineach case via a double bond. In general, in this case A₁ is C and A₅ isN. The remaining groups A₂, A₃ and A₄ are in this case independently ofone another N or C—R^(3a). These include, for example, the compounds ofthe formulae I.a, I.b and I.c:

Among these, preference is given to compounds in which A₁ is C, A₂ andA₅ are N and the remaining groups A₃ and A₄ independently of one anotherare N or C—R^(3a), for example the compounds of the formulae I.b andI.c.

A further preferred embodiment of the present invention relates tocompounds of the formula I in which A₂ is attached to A₃ and A₄ to A₅ ineach case via a double bond. In this case, A₁ is generally N or C—R³ andA₅ is C. Examples are compounds I where A₂ and A₃ are C—R^(3a) and A₄ isN or C—R^(3a), for example the compounds of the formulae I.d and I.e. A₁is preferably N.

Among the compounds of the formula I where A₂ is attached to A₃ and A₄to A₅ in each case via a double bond, A₁ is N and A₅ is C, preference isgiven to those compounds in which A₃ is N and A₂ and A₄ independently ofone another are C—R^(3a) or N. These include, for example, the compoundsof the formulae I.f, I.g, I.h and I.k:

A further preferred embodiment of the present invention relates tocompounds of the formula I in which A₁ is attached to A₅ and A₂ to A₃ orA₁ to A₅ and A₃ to A₄ in each case via a double bond. In general, A₁ andA₅ are then C. Among these, preference is given to compounds I in whichone of the variables A₂ or A₄ is S and the remaining variables A₂, A₃and A₄ independently of one another are N or C—R^(3a), for example thecompounds of the formulae I.m, I.n, I.o, I.p, I.q, I.r, I.s and I.t.

Among these, preference is also given to compounds I in which one of thevariables A₂ or A₄ is N—R⁴ and the remaining variables A₂, A₃ and A₄independently of one another are N or C—R^(3a), for example thecompounds of the formulae I.u and I.v.

In the formulae I.a to I.v, the variables R^(a), n, R¹, R², R³, R^(3a)and R⁴ are as defined above and have in particular the meaningsindicated below as being preferred. R^(3a′) and R^(3a″) are as definedfor R^(3a).

Among the compounds of formulae I.a to I.v, the compounds I.c, I.f, I.gand I.k are especially preferred. Also preferred are the compounds offormulae I.m, I.n, I.o, I.p, I.q, I.r, I.s, I.t, I.u and I.v.

With a view to the use of the compounds I according to the invention asfungicides, the variables n, R^(a), R¹ and R², independently of oneanother and preferably in combination, have the following meanings:

-   n is 1, 2, 3 or 4, in particular 2 or 3;-   R^(a) is halogen, in particular fluorine or chlorine, C₁-C₄-alkyl,    in particular methyl, alkoxy, in particular methoxy,    C₁-C₂-fluoroalkyl, in particular difluoromethyl and trifluoromethyl,    and C₁-C₂-fluoroalkoxy, in particular difluoromethoxy and    trifluoromethoxy. Particularly preferably, R^(a) is selected from    the group consisting of halogen, especially fluorine or chlorine,    C₁-C₄-alkyl, especially methyl, and C₁-C₄-alkoxy, especially    methoxy.-   R¹ is C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl,    C₃-C₈-cycloalkenyl or in particular a group NR⁷R⁸.-   R² is halogen, especially chlorine, or C₁-C₄-alkyl, especially    methyl.

If R¹ is C₁-C₆-alkyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkenyl,C₂-C₆-alkenyl or C₂-C₆-alkynyl, R² is preferably C₁-C₄-alkyl andespecially methyl.

If R¹ is a group NR⁷R⁸, R² is preferably selected from those consistingof chlorine and C₁-C₄-alkyl and especially from a group consisting ofchlorine and methyl.

If R¹ is a group NR⁷R⁸, at least one of the radicals R⁷, R⁸ ispreferably different from hydrogen. In particular, R⁷ is C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl. R⁸ is in particularhydrogen or C₁-C₆-alkyl.

The preferred groups NR⁷R⁸ include those which are a saturated orpartially unsaturated heterocyclic radical which may in addition to thenitrogen atom, have one further heteroatom selected from the groupconsisting of O, S and NR¹⁰ as ring member and which may have 1 or 2substituents selected from the group consisting of C₁-C₆-alkyl andC₁-C₆-haloalkyl. Preferably, the heterocyclic radical has 5 to 7 atomsas ring members. Examples of such heterocyclic radicals are pyrrolidine,piperidine, morpholine, tetrahydropyridine, for example1,2,3,6-tetrahydropyridine, piperazine and azepane, which may besubstituted in the manner indicated above.

With a view to the use of the compounds I according to the invention asfungicides, the radical

is preferably a radical of the formula

in which

-   R^(a1) is fluorine, chlorine or methyl;-   R^(a2) is hydrogen or fluorine;-   R^(a3) is hydrogen, fluorine, chlorine, C₁-C₄-alkyl, especially    methyl, or C₁-C₄-alkoxy, especially methoxy;-   R^(a4) is hydrogen or fluorine;-   R^(a5) is hydrogen, fluorine, chlorine or C₁-C₄-alkyl, especially    methyl.

Here, at least one of the radicals R^(a3), R^(a5) is different fromhydrogen. In particular, at least one and with particular preferenceboth radicals R^(a2), R^(a4) are hydrogen.

Moreover, the variables R³, R^(3a), R^(3a′), R^(3a″), R⁴, R⁵ and R⁶independently of one another and preferably in combination with thepreferred meanings of the variables n, R^(a), R¹ and R² have thefollowing meanings:

R³ is hydrogen;

R^(3a) is hydrogen;

R^(3a′) is hydrogen or CN;

R^(a″) is hydrogen;

R⁴ is C₁-C₄-alkyl;

R⁵ is hydrogen, C₁-C₄-alkyl or C₁-C₄-alkoxy;

R⁶ is hydrogen, C₁-C₄-alkyl or C₁-C₄-alkylcarbonyl.

R¹⁰ is preferably H or C₁-C₄-alkyl, e.g. methyl. R¹¹ and R¹² are,independently of one another, H or methyl, in particular H. R¹³, R¹⁵ andR¹⁶ are preferably C₁-C₄-alkyl, R¹⁴ and R¹⁷ are preferably C₁-C₄-alkyl.

Particularly preferred compounds of the formula I are the compounds ofthe formula I.c in which R² is chlorine or methyl and (R^(a))_(n) is2-fluoro-6-chloro (compounds I.c.1). Examples of these are compoundsI.c.1 in which R² is chlorine, R^(3a′) is hydrogen, R¹ is NR⁷R⁸, whereR⁷, R⁸ together have in each case the meanings given in one row of TableA, or R¹ has the meaning given in one row of Table B. Examples alsoinclude compounds I.c.1 in which R² is methyl, R^(3a′) is hydrogen, R¹is NR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given inone row of Table A, or R¹ has the meaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.c in which R² is chlorine or methyl and(R^(a)), is 2,6-difluoro (compounds I.c.2). Examples of these arecompounds I.c.2 in which R² is chlorine, R^(3a′) is hydrogen, R¹ isNR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given in onerow of Table A, or R¹ has the meaning given in one row of Table B.Examples also include compounds I.c.2 in which R² is methyl, R^(3a′) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.c in which R² is chlorine or methyl and(R^(a)), is 2,6-dichloro (compounds I.c.3). Examples of these arecompounds I.c.3 in which R² is chlorine, R^(3a′) is hydrogen, R¹ isNR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given in onerow of Table A, or R¹ has the meaning given in one row of Table B.Examples also include compounds I.c.3 in which R² is methyl, R^(3a′) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.c in which R² is chlorine or methyl and(R^(a))_(n) is 2-fluoro-6-methyl (compounds I.c.4). Examples of theseare compounds I.c.4 in which R² is chlorine, R^(3a′) is hydrogen, R¹ isNR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given in onerow of Table A, or R¹ has the meaning given in one row of Table B.Examples also include compounds I.c.4 in which R² is methyl, R^(3a′) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.c in which R² is chlorine or methyl and(R^(a))_(n) is 2,4,6-trifluoro (compounds I.c.5). Examples of these arecompounds I.c.5 in which R² is chlorine, R^(3a′) is hydrogen, R¹ isNR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given in onerow of Table A, or R¹ has the meaning given in one row of Table B.Examples also include compounds I.c.5 in which R² is methyl, R^(3a′) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.c in which R² is chlorine or methyl and(R^(a))_(n) is 2,6-difluoro-4-methoxy (compounds I.c.6). Examples ofthese are compounds I.c.6 in which R² is chlorine, R^(3a′) is hydrogen,R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case the meanings givenin one row of Table A, or R¹ has the meaning given in one row of TableB. Examples also include compounds I.c.6 in which R² is methyl, R^(3a′)is hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.c in which R² is chlorine or methyl and(R^(a))_(n) is 2-methyl-4-fluoro (compounds I.c.7). Examples of theseare compounds I.c.7 in which R² is chlorine, R^(3a′) is hydrogen, R¹ isNR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given in onerow of Table A, or R¹ has the meaning given in one row of Table B.Examples also include compounds I.c.7 in which R² is methyl, R^(3a′) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.c in which R² is chlorine or methyl and(R^(a)), is 2-fluoro (compounds I.c.8). Examples of these are compoundsI.c.8 in which R² is chlorine, R^(3a′) is hydrogen, R¹ is NR⁷R⁸, whereR⁷, R⁸ together have in each case the meanings given in one row of TableA, or R¹ has the meaning given in one row of Table B. Examples alsoinclude compounds I.c.8 in which R² is methyl, R^(3a′) is hydrogen, R¹is NR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given inone row of Table A, or R¹ has the meaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.c in which R² is chlorine or methyl and(R^(a))_(n) is 2-chloro (compounds I.c.9). Examples of these arecompounds I.c.9 in which R² is chlorine, R^(3a′) is hydrogen, R¹ isNR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given in onerow of Table A, or R¹ has the meaning given in one row of Table B.Examples also include compounds I.c.9 in which R² is methyl, R^(3a′) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.c in which R² is chlorine or methyl and(R^(a))_(n) is 2,4-difluoro (compounds I.c.10). Examples of these arecompounds I.c.10 in which R² is chlorine, R^(3a′) is hydrogen, R¹ isNR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given in onerow of Table A, or R¹ has the meaning given in one row of Table B.Examples also include compounds I.c.10 in which R² is methyl, R^(3a′) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.c in which R² is chlorine or methyl and(R^(a)), is 2-fluoro-4-chloro (compounds I.c.11). Examples of these arecompounds I.c.11 in which R² is chlorine, R^(3a′) is hydrogen, R¹ isNR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given in onerow of Table A, or R¹ has the meaning given in one row of Table B.Examples also include compounds I.c.11 in which R² is methyl, R^(3a′) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.c in which R² is chlorine or methyl and(R^(a))_(n) is 2-chloro-4-fluoro (compounds I.c.12). Examples of theseare compounds I.c.12 in which R² is chlorine, R^(3a′) is hydrogen, R¹ isNR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given in onerow of Table A, or R¹ has the meaning given in one row of Table B.Examples also include compounds I.c.12 in which R² is methyl, R^(3a′) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.c in which R² is chlorine or methyl and(R^(a))_(n) is 2-methyl (compounds I.c.13). Examples of these arecompounds I.c.13 in which R² is chlorine, R^(3a′) is hydrogen, R¹ isNR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given in onerow of Table A, or R¹ has the meaning given in one row of Table B.Examples also include compounds I.c.13 in which R² is methyl, R^(3a′) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.c in which R² is chlorine or methyl and(R^(a))_(n) is 2,4-dimethyl (compounds I.c.14). Examples of these arecompounds I.c.14 in which R² is chlorine, R^(3a′) is hydrogen, R¹ isNR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given in onerow of Table A, or R¹ has the meaning given in one row of Table B.Examples also include compounds I.c.14 in which R² is methyl, R^(3a′) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.c in which R² is chlorine or methyl and(R^(a))_(n) is 2-fluoro-4-methyl (compounds I.c.15). Examples of theseare compounds I.c.15 in which R² is chlorine, R^(3a′) is hydrogen, R¹ isNR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given in onerow of Table A, or R¹ has the meaning given in one row of Table B.Examples also include compounds I.c.15 in which R² is methyl, R^(3a′) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.c in which R² is chlorine or methyl and(R^(a))_(n) is 2,6-dimethyl (compounds I.c.16). Examples of these arecompounds I.c.16 in which R² is chlorine, R^(3a′) is hydrogen, R¹ isNR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given in onerow of Table A, or R¹ has the meaning given in one row of Table B.Examples also include compounds I.c.16 in which R² is methyl, R^(3a′) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B.

Particularly preferred compounds of the formula I are the compounds ofthe formula I.f in which R² is chlorine or methyl and (R^(a))_(n) is2-fluoro-6-chloro (compounds I.f.1). Examples of these are compoundsI.f.1 in which R² is chlorine, R^(3a′) and R^(3a″) are hydrogen, R¹ isNR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given in onerow of Table A, or R¹ has the meaning given in one row of Table B.Examples also include compounds I.f.1 in which R² is methyl, R^(3a′) andR^(3a″) are hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in eachcase the meanings given in one row of Table A, or R¹ has the meaninggiven in one row of Table B. Examples also include compounds I.f.1 inwhich R² is chlorine, R^(3a′) is CN, R^(3a″) is hydrogen, R¹ is NR⁷R⁸,where R⁷, R⁸ together have in each case the meanings given in one row ofTable A, or R¹ has the meaning given in one row of Table B. Examplesalso include compounds I.f.1 in which R² is methyl, R^(3a′) is CN,R^(3a″) is hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in eachcase the meanings given in one row of Table A, or R¹ has the meaninggiven in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.f in which R² is chlorine or methyl and(R^(a))_(n) is 2,6-difluoro (compounds I.f.2). Examples of these arecompounds I.f.2 in which R² is chlorine, R^(3a′) and R^(3a″) arehydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B. Examples also include compounds I.f.2 in which R² ismethyl, R^(3a′) and R^(3a″) are hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B. Examples also includecompounds I.f.2 in which R² is chlorine, R^(3a′) is CN, R^(3a″) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B. Examples also include compounds I.f.2 in which R² ismethyl, R^(3a′) is CN, R^(3a″) is hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.f in which R² is chlorine or methyl and(R^(a))_(n) is 2,6-dichloro (compounds I.f.3). Examples of these arecompounds I.f.3 in which R² is chlorine, R^(3a′) and R^(3a″) arehydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B. Examples also include compounds I.f.3 in which R² ismethyl, R^(3a′) and R^(3a″) are hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B. Examples also includecompounds I.f.3 in which R² is chlorine, R^(3a′) is CN, R^(3a″) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B. Examples also include compounds I.f.3 in which R² ismethyl, R^(3a′) is CN, R^(3a″) is hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.f in which R² is chlorine or methyl and(R^(a))_(n) is 2-fluoro-6-methyl (compounds I.f.4). Examples of theseare compounds I.f.4 in which R² is chlorine, R^(3a′) and R^(3a″) arehydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B. Examples also include compounds I.f.4 in which R² ismethyl, R^(3a′) and R^(3a″) are hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B. Examples also includecompounds I.f.4 in which R² is chlorine, R^(3a′) is CN, R^(3a″) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B. Examples also include compounds I.f.4 in which R² ismethyl, R^(3a′) is CN, R^(3a″) is hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.f in which R² is chlorine or methyl and(R^(a))_(n) is 2,4,6-trifluoro (compounds I.f.5). Examples of these arecompounds I.f.5 in which R² is chlorine, R^(3a′) and R^(3a″) arehydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B. Examples also include compounds I.f.5 in which R² ismethyl, R^(3a′) and R^(3a″) are hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B. Examples also includecompounds I.f.5 in which R² is chlorine, R^(3a′) is CN, R^(3a″) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B. Examples also include compounds I.f.5 in which R² ismethyl, R^(3a′) is CN, R^(3a″) is hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.f in which R² is chlorine or methyl and(R^(a))_(n) is 2,6-difluoro-4-methoxy (compounds I.f.6). Examples ofthese are compounds I.f.6 in which R² is chlorine, R^(3a′) and R^(3a″)are hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B. Examples also include compounds I.f.6 in which R² ismethyl, R^(3a′) and R^(3a″) are hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B. Examples also j includecompounds I.f.6 in which R² is chlorine, R^(3a′) is CN, R^(3a″) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B. Examples also include compounds I.f.6 in which R² ismethyl, R^(3a′) is CN, R^(3a″) is hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.f in which R² is chlorine or methyl and(R^(a)), is 2-methyl-4-fluoro (compounds I.f.7). Examples of these arecompounds I.f.7 in which R² is chlorine, R^(3a′) and R^(3a″) arehydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B. Examples also include compounds I.f.7 in which R² ismethyl, R^(3a′) and R^(3a″) are hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B. Examples also includecompounds I.f.7 in which R² is chlorine, R^(3a′) is CN, R^(3a″) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B. Examples also include compounds I.f.7 in which R² ismethyl, R^(3a′) is CN, R^(3a″) is hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.f in which R² is chlorine or methyl and(R^(a))_(n) is 2-fluoro (compounds I.f.8). Examples of these arecompounds I.f.8 in which R² is chlorine, R^(3a′) and R^(3a″) arehydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B. Examples also include compounds I.f.8 in which R² ismethyl, R^(3a′) and R^(3a″) are hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B. Examples also includecompounds I.f.8 in which R² is chlorine, R^(3a′) is CN, R^(3a″) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B. Examples also include compounds I.f.8 in which R² ismethyl, R^(3a′) is CN, R^(3a″) is hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.f in which R² is chlorine or methyl and(R^(a))_(n) is 2-chloro (compounds I.f.9). Examples of these arecompounds I.f.9 in which R² is chlorine, R^(3a′) and R^(3a″) arehydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B. Examples also include compounds I.f.9 in which R² ismethyl, R^(3a′) and R^(3a″) are hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B. Examples also includecompounds I.f.9 in which R² is chlorine, R^(3a′) is CN, R^(3a″) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B. Examples also include compounds I.f.9 in which R² ismethyl, R^(3a′) is CN, R^(3a″) is hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.f in which R² is chlorine or methyl and(R^(a))_(n) is 2,4-difluoro (compounds I.f.10). Examples of these arecompounds I.f.10 in which R² is chlorine, R^(3a′) and R^(3a″) arehydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B. Examples also include compounds I.f.10 in which R² ismethyl, R^(3a′) and R^(3a″) are hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B. Examples also includecompounds I.f.10 in which R² is chlorine, R^(3a′) is CN, R^(3a″) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B. Examples also include compounds I.f.10 in which R² ismethyl, R^(3a′) is CN, R^(3a″) is hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.f in which R² is chlorine or methyl and(R^(a))_(n) is 2-fluoro-4-chloro (compounds I.f.11). Examples of theseare compounds I.f.11 in which R² is chlorine, R^(3a′) and R^(3a″) arehydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B. Examples also include compounds I.f.11 in which R² ismethyl, R^(3a′) and R^(3a″) are hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B. Examples also includecompounds I.f.11 in which R² is chlorine, R^(3a′) is CN, R^(3a″) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B. Examples also include compounds I.f.11 in which R² ismethyl, R^(3a′) is CN, R^(3a″) is hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.f in which R² is chlorine or methyl and(R^(a))_(n) is 2-chloro-4-fluoro (compounds I.f.12). Examples of theseare compounds I.f.12 in which R² is chlorine, R^(3a′) and R^(3a″) arehydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B. Examples also include compounds I.f.12 in which R² ismethyl, R^(3a′) and R^(3a″) are hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B. Examples also includecompounds I.f.12 in which R² is chlorine, R^(3a′) is CN, R^(3a″) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B. Examples also include compounds I.f.12 in which R² ismethyl, R^(3a′) is CN, R^(3a″) is hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.f in which R² is chlorine or methyl and(R^(a))_(n) is 2-methyl (compounds I.f.13). Examples of these arecompounds I.f.13 in which R² is chlorine, R^(3a′) and R^(3a″) arehydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B. Examples also include compounds I.f.13 in which R² ismethyl, R^(3a′) and R^(3a″) are hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B. Examples also includecompounds I.f.13 in which R² is chlorine, R^(3a′) is CN, R^(3a″) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B. Examples also include compounds I.f.13 in which R² ismethyl, R^(3a′) is CN, R^(3a″) is hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.f in which R² is chlorine or methyl and(R^(a))_(n) is 2,4-dimethyl (compounds I.f.14). Examples of these arecompounds I.f.14 in which R² is chlorine, R^(3a′) and R^(3a″) arehydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B. Examples also include compounds I.f.14 in which R² ismethyl, R^(3a′) and R^(3a″) are hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B. Examples also includecompounds I.f.14 in which R² is chlorine, R^(3a′) is CN, R^(3a″) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B. Examples also include compounds I.f.14 in which R² ismethyl, R^(3a′) is CN, R^(3a″) is hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.f in which R² is chlorine or methyl and(R^(a))_(n) is 2-fluoro-4-methyl (compounds I.f.15). Examples of theseare compounds I.f.15 in which R² is chlorine, R^(3a′) and R^(3a″) arehydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B. Examples also include compounds I.f.15 in which R² ismethyl, R^(3a′) and R^(3a″) are hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B. Examples also includecompounds I.f.15 in which R² is chlorine, R^(3a′) is CN, R^(3a″) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B. Examples also include compounds I.f.15 in which R² ismethyl, R^(3a′) is CN, R^(3a″) is hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.f in which R² is chlorine or methyl and(R^(a))_(n) is 2,6-dimethyl (compounds I.f.16). Examples of these arecompounds I.f.16 in which R² is chlorine, R^(3a′) and R^(3a″) arehydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B.

Examples also include compounds I.f.16 in which R² is methyl, R^(3a′)and R^(3a″) are hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have ineach case the meanings given in one row of Table A, or R¹ has themeaning given in one row of Table B. Examples also include compoundsI.f.16 in which R² is chlorine, R^(3a′) is CN, R^(3a″) is hydrogen, R¹is NR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given inone row of Table A, or R¹ has the meaning given in one row of Table B.Examples also include compounds I.f.16 in which R² is methyl, R^(3a′) isCN, R^(3a″) is hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in eachcase the meanings given in one row of Table A, or R¹ has the meaninggiven in one row of Table B.

Particularly preferred compounds of the formula I are the compounds ofthe formula I.g in which R² is chlorine or methyl and (R^(a))_(n) is2-fluoro-6-chloro (compounds I.g.1). Examples of these are compoundsI.g.1 in which R² is chlorine, R^(3a″) is hydrogen, R¹ is NR⁷R⁸, whereR⁷, R⁸ together have in each case the meanings given in one row of TableA, or R¹ has the meaning given in one row of Table B. Examples alsoinclude compounds I.g.1 in which R² is methyl, R^(3a″) is hydrogen, R¹is NR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given inone row of Table A, or R¹ has the meaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.g in which R² is chlorine or methyl and(R^(a))_(n) is 2,6-difluoro (compounds I.g.2). Examples of these arecompounds I.g.2 in which R² is chlorine, R^(3″) is hydrogen, R¹ isNR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given in onerow of Table A, or R¹ has the meaning given in one row of Table B.Examples also include compounds I.g.2 in which R² is methyl, R^(3a″) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.g in which R² is chlorine or methyl and(R^(a))_(n) is 2,6-dichloro (compounds I.g.3). Examples of these arecompounds I.g.3 in which R² is chlorine, R^(3a″) is hydrogen, R¹ isNR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given in onerow of Table A, or R¹ has the meaning given in one row of Table B.Examples also include compounds I.g.3 in which R² is methyl, R^(3a″) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.g in which R² is chlorine or methyl and(R^(a))_(n) is 2-fluoro-6-methyl (compounds I.g.4). Examples of theseare compounds I.g.4 in which R² is chlorine, R^(3″) is hydrogen, R¹ isNR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given in onerow of Table A, or R¹ has the meaning given in one row of Table B.Examples also include compounds I.g.4 in which R² is methyl, R^(3a″) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.g in which R² is chlorine or methyl and(R^(a))_(n) is 2,4,6-trifluoro (compounds I.g.5). Examples of these arecompounds I.g.5 in which R² is chlorine, R^(3a″), is hydrogen, R¹ isNR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given in onerow of Table A, or R¹ has the meaning given in one row of Table B.Examples also include compounds I.g.5 in which R² is methyl, R^(3a″) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.g in which R² is chlorine or methyl and(R^(a))_(n) is 2,6-difluoro-4-methoxy (compounds I.g.6). Examples ofthese are compounds I.g.6 in which R² is chlorine, R^(3a″) is hydrogen,R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case the meanings givenin one row of Table A, or R¹ has the meaning given in one row of TableB. Examples also include compounds I.g.6 in which R² is methyl, R^(3a″)is hydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.g in which R² is chlorine or methyl and(R^(a))_(n) is 2-methyl-4-fluoro (compounds I.g.7). Examples of theseare compounds I.g.7 in which R² is chlorine, R^(3a″) is hydrogen, R¹ isNR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given in onerow of Table A, or R¹ has the meaning given in one row of Table B.Examples also include compounds I.g.7 in which R² is methyl, R^(3a″) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.g in which R² is chlorine or methyl and(R^(a))_(n) is 2-fluoro (compounds I.g.8). Examples of these arecompounds I.g.8 in which R² is chlorine, R^(3a″) is hydrogen, R¹ isNR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given in onerow of Table A, or R¹ has the meaning given in one row of Table B.Examples also include compounds I.g.8 in which R² is methyl, R^(3a″) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.g in which R² is chlorine or methyl and(R^(a))_(n) is 2-chloro (compounds I.g.9). Examples of these arecompounds I.g.9 in which R² is chlorine, R^(3a″) is hydrogen, R¹ isNR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given in onerow of Table A, or R¹ has the meaning given in one row of Table B.Examples also include compounds I.g.9 in which R² is methyl, R^(3a″) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.g in which R² is chlorine or methyl and(R^(a))_(n) is 2,4-difluoro (compounds I.g.10). Examples of these arecompounds I.g.10 in which R² is chlorine, R^(3a″) is hydrogen, R¹ isNR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given in onerow of Table A, or R¹ has the meaning given in one row of Table B.Examples also include compounds I.g.10 in which R² is methyl, R^(3a″) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.g in which R² is chlorine or methyl and(R^(a))_(n) is 2-fluoro-4-chloro (compounds I.g.11). Examples of theseare compounds I.g.11 in which R² is chlorine, R^(3a″) is hydrogen, R¹ isNR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given in onerow of Table A, or R¹ has the meaning given in one row of Table B.Examples also include compounds I.g.11 in which R² is methyl, R^(3a″) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.g in which R² is chlorine or methyl and(R^(a))_(n) is 2-chloro-4-fluoro (compounds I.g.12). Examples of theseare compounds I.g.12 in which R² is chlorine, R^(3a″) is hydrogen, R¹ isNR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given in onerow of Table A, or R¹ has the meaning given in one row of Table B.Examples also include compounds I.g.12 in which R² is methyl, R^(3a″) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.g in which R² is chlorine or methyl and(R^(a))_(n) is 2-methyl (compounds I.g.13). Examples of these arecompounds I.g.13 in which R² is chlorine, R^(3a″) is hydrogen, R¹ isNR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given in onerow of Table A, or R¹ has the meaning given in one row of Table B.Examples also include compounds I.g.13 in which R² is methyl, R^(3a″) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.g in which R² is chlorine or methyl and(R^(a))_(n) is 2,4-dimethyl (compounds I.g.14). Examples of these arecompounds I.g.14 in which R² is chlorine, R^(3a″) is hydrogen, R¹ isNR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given in onerow of Table A, or R¹ has the meaning given in one row of Table B.Examples also include compounds I.g.14 in which R² is methyl, R^(3a″) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.g in which R² is chlorine or methyl and(R^(a))_(n) is 2-fluoro-4-methyl (compounds I.g.15). Examples of theseare compounds I.g.15 in which R² is chlorine, R^(3a″) is hydrogen, R¹ isNR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given in onerow of Table A, or R¹ has the meaning given in one row of Table B.Examples also include compounds I.g.15 in which R² is methyl, R^(3a″) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.g in which R² is chlorine or methyl and(R^(a))_(n) is 2,6-dimethyl (compounds I.g.16). Examples of these arecompounds I.g.16 in which R² is chlorine, R^(3a″) is hydrogen, R¹ isNR⁷R⁸, where R⁷, R⁸ together have in each case the meanings given in onerow of Table A, or R¹ has the meaning given in one row of Table B.Examples also include compounds I.g.16 in which R² is methyl, R^(3a″) ishydrogen, R¹ is NR⁷R⁸, where R⁷, R⁸ together have in each case themeanings given in one row of Table A, or R¹ has the meaning given in onerow of Table B.

Particularly preferred compounds of the formula I are the compounds ofthe formula I.k in which R² is chlorine or methyl and (R^(a))_(n) is2-fluoro-6-chloro (compounds I.k.1). Examples of these are compoundsI.k.1 in which R² is chlorine, R¹ is NR⁷R⁸, where R⁷, R⁸ together havein each case the meanings given in one row of Table A, or R¹ has themeaning given in one row of Table B. Examples also include compoundsI.k.1 in which R² is methyl, R¹ is NR⁷R⁸, where R⁷, R⁸ together have ineach case the meanings given in one row of Table A, or R¹ has themeaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.k in which R² is chlorine or methyl and(R^(a))_(n) is 2,6-difluoro (compounds I.k.2). Examples of these arecompounds I.k.2 in which R² is chlorine, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B. Examples also includecompounds I.k.2 in which R² is methyl, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.k in which R² is chlorine or methyl and(R^(a))_(n) is 2,6-dichloro (compounds I.k.3). Examples of these arecompounds I.k.3 in which R² is chlorine, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B. Examples also includecompounds I.k.3 in which R² is methyl, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.k in which R² is chlorine or methyl and(R^(a))_(n) is 2-fluoro-6-methyl (compounds I.k.4). Examples of theseare compounds I.k.4 in which R² is chlorine, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B. Examples also includecompounds I.k.4 in which R² is methyl, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.k in which R² is chlorine or methyl and(R^(a))_(n) is 2,4,6-trifluoro (compounds I.k.5). Examples of these arecompounds I.k.5 in which R² is chlorine, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B. Examples also includecompounds I.k.5 in which R² is methyl, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.k in which R² is chlorine or methyl and(R^(a))_(n) is 2,6-difluoro-4-methoxy (compounds I.k.6). Examples ofthese are compounds I.k.6 in which R² is chlorine, R¹ is NR⁷R⁸, whereR⁷, R⁸ together have in each case the meanings given in one row of TableA, or R¹ has the meaning given in one row of Table B. Examples alsoinclude compounds I.k.⁶ in which R² is methyl, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.k in which R² is chlorine or methyl and(R^(a))_(n) is 2-methyl-4-fluoro (compounds I.k.7). Examples of theseare compounds I.k.7 in which R² is chlorine, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B. Examples also includecompounds I.k.7 in which R² is methyl, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.k in which R² is chlorine or methyl and(R^(a))_(n) is 2-fluoro (compounds I.k.8). Examples of these arecompounds I.k.8 in which R² is chlorine, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B. Examples also includecompounds I.k.8 in which R² is methyl, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.k in which R² is chlorine or methyl and(R^(a))_(n) is 2-chloro (compounds I.k.9). Examples of these arecompounds I.k.9 in which R² is chlorine, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B. Examples also includecompounds I.k.9 in which R² is methyl, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.k in which R² is chlorine or methyl and(R^(a))_(n) is 2,4-difluoro (compounds I.k.10). Examples of these arecompounds I.k.10 in which R² is chlorine, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B. Examples also includecompounds I.k.10 in which R² is methyl, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.k in which R² is chlorine or methyl and(R^(a))_(n) is 2-fluoro-4-chloro (compounds I.k.11). Examples of theseare compounds I.k.11 in which R² is chlorine, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B. Examples also includecompounds I.k.11 in which R² is methyl, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.k in which R² is chlorine or methyl and(R^(a))_(n) is 2-chloro-4-fluoro (compounds I.k.12). Examples of theseare compounds I.k.12 in which R² is chlorine, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B. Examples also includecompounds I.k.12 in which R² is methyl, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.k in which R² is chlorine or methyl and(R^(a))_(n) is 2-methyl (compounds I.k.13). Examples of these arecompounds I.k.13 in which R² is chlorine, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B. Examples also includecompounds I.k.13 in which R² is methyl, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.k in which R² is chlorine or methyl and(R^(a))_(n) is 2,4-dimethyl (compounds I.k.14). Examples of these arecompounds I.k.14 in which R² is chlorine, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B. Examples also includecompounds I.k.14 in which R² is methyl, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.k in which R² is chlorine or methyl and(R^(a))_(n) is 2-fluoro-4-methyl (compounds I.k.15). Examples of theseare compounds I.k.15 in which R² is chlorine, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B. Examples also includecompounds I.k.15 in which R² is methyl, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B.

Particularly preferred compounds of the formula I are further thecompounds of the formula I.k in which R² is chlorine or methyl and(R^(a))_(n) is 2,6-dimethyl (compounds I.k.16). Examples of these arecompounds I.k.16 in which R² is chlorine, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B. Examples also includecompounds I.k.16 in which R² is methyl, R¹ is NR⁷R⁸, where R⁷, R⁸together have in each case the meanings given in one row of Table A, orR¹ has the meaning given in one row of Table B. TABLE A No. R⁷ R⁸ A-1 HH A-2 CH₂CH₃ H A-3 CH₂CH₃ CH₃ A-4 CH₂CH₃ CH₂CH₃ A-5 CH₂CF₃ H A-6 CH₂CF₃CH₃ A-7 CH₂CF₃ CH₂CH₃ A-8 CH₂CCl₃ H A-9 CH₂CCl₃ CH₃ A-10 CH₂CCl₃ CH₂CH₃A-11 CH₂CH₂CH₃ H A-12 CH₂CH₂CH₃ CH₃ A-13 CH₂CH₂CH₃ CH₂CH₃ A-14 CH₂CH₂CH₃CH₂CH₂CH₃ A-15 CH(CH₃)₂ H A-16 CH(CH₃)₂ CH₃ A-17 CH(CH₃)₂ CH₂CH₃ A-18(±) CH(CH₃)—CH₂CH₃ H A-19 (±) CH(CH₃)—CH₂CH₃ CH₃ A-20 (±) CH(CH₃)—CH₂CH₃CH₂CH₃ A-21 (S) CH(CH₃)—CH₂CH₃ H A-22 (S) CH(CH₃)—CH₂CH₃ CH₃ A-23 (S)CH(CH₃)—CH₂CH₃ CH₂CH₃ A-24 (R) CH(CH₃)—CH₂CH₃ H A-25 (R) CH(CH₃)—CH₂CH₃CH₃ A-26 (R) CH(CH₃)—CH₂CH₃ CH₂CH₃ A-27 (±) CH(CH₃)—CH(CH₃)₂ H A-28 (±)CH(CH₃)—CH(CH₃)₂ CH₃ A-29 (±) CH(CH₃)—CH(CH₃)₂ CH₂CH₃ A-30 (S)CH(CH₃)—CH(CH₃)₂ H A-31 (S) CH(CH₃)—CH(CH₃)₂ CH₃ A-32 (S)CH(CH₃)—CH(CH₃)₂ CH₂CH₃ A-33 (R) CH(CH₃)—CH(CH₃)₂ H A-34 (R)CH(CH₃)—CH(CH₃)₂ CH₃ A-35 (R) CH(CH₃)—CH(CH₃)₂ CH₂CH₃ A-36 (±)CH(CH₃)—C(CH₃)₃ H A-37 (±) CH(CH₃)—C(CH₃)₃ CH₃ A-38 (±) CH(CH₃)—C(CH₃)₃CH₂CH₃ A-39 (S) CH(CH₃)—C(CH₃)₃ H A-40 (S) CH(CH₃)—C(CH₃)₃ CH₃ A-41 (S)CH(CH₃)—C(CH₃)₃ CH₂CH₃ A-42 (R) CH(CH₃)—C(CH₃)₃ H A-43 (R)CH(CH₃)—C(CH₃)₃ CH₃ A-44 (R) CH(CH₃)—C(CH₃)₃ CH₂CH₃ A-45 (±) CH(CH₃)—CF₃H A-46 (±) CH(CH₃)—CF₃ CH₃ A-47 (±) CH(CH₃)—CF₃ CH₂CH₃ A-48 (S)CH(CH₃)—CF₃ H A-49 (S) CH(CH₃)—CF₃ CH₃ A-50 (S) CH(CH₃)—CF₃ CH₂CH₃ A-51(R) CH(CH₃)—CF₃ H A-52 (R) CH(CH₃)—CF₃ CH₃ A-53 (R) CH(CH₃)—CF₃ CH₂CH₃A-54 (±) CH(CH₃)—CCl₃ H A-55 (±) CH(CH₃)—CCl₃ CH₃ A-56 (±) CH(CH₃)—CCl₃CH₂CH₃ A-57 (S) CH(CH₃)—CCl₃ H A-58 (S) CH(CH₃)—CCl₃ CH₃ A-59 (S)CH(CH₃)—CCl₃ CH₂CH₃ A-60 (R) CH(CH₃)—CCl₃ H A-61 (R) CH(CH₃)—CCl₃ CH₃A-62 (R) CH(CH₃)—CCl₃ CH₂CH₃ A-63 CH₂CF₂CF₃ H A-64 CH₂CF₂CF₃ CH₃ A-65CH₂CF₂CF₃ CH₂CH₃ A-66 CH₂(CF₂)₂CF₃ H A-67 CH₂(CF₂)₂CF₃ CH₃ A-68CH₂(CF₂)₂CF₃ CH₂CH₃ A-69 CH₂C(CH₃)═CH₂ H A-70 CH₂C(CH₃)═CH₂ CH₃ A-71CH₂C(CH₃)═CH₂ CH₂CH₃ A-72 CH₂CH═CH₂ H A-73 CH₂CH═CH₂ CH₃ A-74 CH₂CH═CH₂CH₂CH₃ A-75 CH(CH₃)CH═CH₂ H A-76 CH(CH₃)CH═CH₂ CH₃ A-77 CH(CH₃)CH═CH₂CH₂CH₃ A-78 CH(CH₃)C(CH₃)═CH₂ H A-79 CH(CH₃)C(CH₃)═CH₂ CH₃ A-80CH(CH₃)C(CH₃)═CH₂ CH₂CH₃ A-81 cyclopentyl H A-82 cyclopentyl CH₃ A-83cyclopentyl CH₂CH₃ A-84 cyclohexyl H A-85 cyclohexyl CH₃ A-86 cyclohexylCH₂CH₃ A-87 —(CH₂)₂CH═CHCH₂— A-88 —(CH₂)₂C(CH₃)═CHCH₂— A-89—(CH₂)₂CH(CH₃)(CH₂)₂— A-90 —(CH₂)₂CHF(CH₂)₂— A-91 —(CH₂)₃CHFCH₂— A-92—(CH₂)₂CH(CF₃)(CH₂)₂— A-93 —(CH₂)₂O(CH₂)₂— A-94 —(CH₂)₂S(CH₂)₂— A-95—(CH₂)₅— A-96 —(CH₂)₄— A-97 —CH₂CH═CHCH₂— A-98 —CH(CH₃)(CH₂)₃— A-99—CH₂CH(CH₃)(CH₂)₂—

TABLE B No. R¹ B-1 CH₃ B-2 CH₂CH₃ B-3 CH₂CH₂CH₃ B-4 CH(CH₃)₂ B-5CH₂CH(CH₃)₂ B-6 (±) CH(CH₃)CH₂CH₃ B-7 (R) CH(CH₃)CH₂CH₃ B-8 (S)CH(CH₃)CH₂CH₃ B-9 (CH₂)₃CH₃ B-10 C(CH₃)₃ B-11 (CH₂)₄CH₃ B-12 CH(CH₂CH₃)₂B-13 CH₂CH₂CH(CH₃)₂ B-14 (±) CH(CH₃)(CH₂)₂CH₃ B-15 (R) CH(CH₃)(CH₂)₂CH₃B-16 (S) CH(CH₃)(CH₂)₂CH₃ B-17 (±) CH₂CH(CH₃)CH₂CH₃ B-18 (R)CH₂CH(CH₃)CH₂CH₃ B-19 (S) CH₂CH(CH₃)CH₂CH₃ B-20 (±) CH(CH₃)CH(CH₃)₂ B-21(R) CH(CH₃)CH(CH₃)₂ B-22 (S) CH(CH₃)CH(CH₃)₂ B-23 (CH₂)₅CH₃ B-24 (±, ±)CH(CH₃)CH(CH₃)CH₂CH₃ B-25 (±, R) CH(CH₃)CH(CH₃)CH₂CH₃ B-26 (±, S)CH(CH₃)CH(CH₃)CH₂CH₃ B-27 (R, ±) CH(CH₃)CH(CH₃)CH₂CH₃ B-28 (S, ±)CH(CH₃)CH(CH₃)CH₂CH₃ B-29 (±) CH₂CH(CH₃)CF₃ B-30 (R) CH₂CH(CH₃)CF₃ B-31(S) CH₂CH(CH₃)CF₃ B-32 (±) CH₂CH(CF₃)CH₂CH₃ B-33 (R) CH₂CH(CF₃)CH₂CH₃B-34 (S) CH₂CH(CF₃)CH₂CH₃ B-35 (±, ±) CH(CH₃)CH(CH₃)CF₃ B-36 (±, R)CH(CH₃)CH(CH₃)CF₃ B-37 (±, S) CH(CH₃)CH(CH₃)CF₃ B-38 (R, ±)CH(CH₃)CH(CH₃)CF₃ B-39 (S, ±) CH(CH₃)CH(CH₃)CF₃ B-40 (±, ±)CH(CH₃)CH(CF₃)CH₂CH₃ B-41 (±, R) CH(CH₃)CH(CF₃)CH₂CH₃ B-42 (±, S)CH(CH₃)CH(CF₃)CH₂CH₃ B-43 (R, ±) CH(CH₃)CH(CF₃)CH₂CH₃ B-44 (S, ±)CH(CH₃)CH(CF₃)CH₂CH₃ B-45 CF₃ B-46 CF₂CF₃ B-47 CF₂CF₂CF₃ B-48 c-C₃H₅B-49 (1-CH₃)-c-C₃H₄ B-50 c-C₅H₉ B-51 c-C₆H₁₁ B-52 (4-CH₃)-c-C₆H₁₀ B-53CH₂C(CH₃)═CH₂ B-54 CH₂CH₂C(CH₃)═CH₂ B-55 CH₂—C(CH₃)₃ B-56 CH₂—Si(CH₃)₃B-57 n-C₆H₁₃ B-58 (CH₂)₃—CH(CH₃)₂ B-59 (CH₂)₂—CH(CH₃)—C₂H₅ B-60CH₂—CH(CH₃)-n-C₃H₇ B-61 CH(CH₃)-n-C₄H₉ B-62 CH₂—CH(C₂H₅)₂ B-63CH(C₂H₅)-n-C₃H₇ B-64 CH₂-c-C₅H₉ B-65 CH₂—CH(CH₃)—CH(CH₃)₂ B-66CH(CH₃)—CH₂CH(CH₃)₂ B-67 CH(CH₃)—CH(CH₃)—C₂H₅ B-68 CH(CH₃)—C(CH₃)₃ B-69(CH₂)₂—C(CH₃)₃ B-70 CH₂—C(CH₃)₂—C₂H₅ B-71 2-CH₃-c-C₅H₈ B-72 3-CH₃-c-C₅H₈B-73 C(CH₃)₂-n-C₃H₇ B-74 (CH₂)₆—CH₃ B-75 (CH₂)₄—CH(CH₃)₂ B-76(CH₂)₃—CH(CH₃)—C₂H₅ B-77 (CH₂)₂—CH(CH₃)-n-C₃H₇ B-78 CH₂—CH(CH₃)-n-C₄H₉B-79 CH(CH₃)-n-C₅H₁₁ B-80 (CH₂)₃C(CH₃)₃ B-81 (CH₂)₂CH(CH₃)—CH(CH₃)₂ B-82(CH₂)CH(CH₃)—CH₂CH(CH₃)₂ B-83 CH(CH₃)(CH₂)₂—CH(CH₃)₂ B-84(CH₂)₂C(CH₃)₂C₂H₅ B-85 CH₂CH(CH₃)CH(CH₃)C₂H₅ B-86 CH(CH₃)CH₂CH(CH₃)C₂H₅B-87 CH₂C(CH₃)₂-n-C₃H₇ B-88 CH(CH₃)CH(CH₃)-n-C₃H₇ B-89 C(CH₃)₂-n-C₄H₉B-90 (CH₂)₂CH(C₂H₅)₂ B-91 CH₂CH(C₂H₅)-n-C₃H₇ B-92 CH(C₂H₅)-n-C₄H₉ B-93CH₂CH(CH₃)C(CH₃)₃ B-94 CH(CH₃)CH₂C(CH₃)₃ B-95 CH₂C(CH₃)₂CH(CH₃)₂ B-96CH₂CH(C₂H₅)CH(CH₃)₂ B-97 CH(CH₃)CH(CH₃)CH(CH₃)₂ B-98 C(CH₃)₂CH₂CH(CH₃)₂B-99 CH(C₂H₅)CH₂CH(CH₃)₂ B-100 CH(CH₃)C(CH₃)₂C₂H₅ B-101 CH(CH₃)CH(C₂H₅)₂B-102 C(CH₃)₂CH(CH₃)C₂H₅ B-103 CH(C₂H₅)CH(CH₃)C₂H₅ B-104C(CH₃)(C₂H₅)-n-C₃H₇ B-105 CH(n-C₃H₇)₂ B-106 CH(n-C₃H₇)CH(CH₃)₂ B-107C(CH₃)₂C(CH₃)₃ B-108 C(CH₃)(C₂H₅)—CH(CH₃)₂ B-109 C(C₂H₅)₃ B-110(3-CH₃)-c-C₆H₁₀ B-111 (2-CH₃)-c-C₆H₁₀ B-112 n-C₈H₁₇ B-113CH₂C(═NO—CH₃)CH₃ B-114 CH₂C(═NO—C₂H₅)CH₃ B-115 CH₂C(═NO-n-C₃H₇)CH₃ B-116CH₂C(═NO-i-C₃H₇)CH₃ B-117 CH(CH₃)C(═NOCH₃)CH₃ B-118 CH(CH₃)C(═NOC₂H₅)CH₃B-119 CH(CH₃)C(═NO-n-C₃H₇)CH₃ B-120 CH(CH₃)C(═NO-i-C₃H₇)CH₃ B-121C(═NOCH₃)C(═NOCH₃)CH₃ B-122 C(═NOCH₃)C(═NOC₂H₅)CH₃ B-123C(═NOCH₃)C(═NO-n-C₃H₇)CH₃ B-124 C(═NOCH₃)C(═NO-i-C₃H₇)CH₃ B-125C(═NOC₂H₅)C(═NOCH₃)CH₃ B-126 C(═NOC₂H₅)C(═NOC₂H₅)CH₃ B-127C(═NOC₂H₅)C(═NO-n-C₃H₇)CH₃ B-128 C(═NOC₂H₅)C(═NO-i-C₃H₇)CH₃ B-129CH₂C(═NO—CH₃)C₂H₅ B-130 CH₂C(═NO—C₂H₅)C₂H₅ B-131 CH₂C(═NO-n-C₃H₇)C₂H₅B-132 CH₂C(═NO-i-C₃H₇)C₂H₅ B-133 CH(CH₃)C(═NOCH₃)C₂H₅ B-134CH(CH₃)C(═NOC₂H₅)C₂H₅ B-135 CH(CH₃)C(═NO-n-C₃H₇)C₂H₅ B-136CH(CH₃)C(═NO-n-C₃H₇)C₂H₅ B-137 C(═NOCH₃)C(═NOCH₃)C₂H₅ B-138C(═NOCH₃)C(═NOC₂H₅)C₂H₅ B-139 C(═NOCH₃)C(═NO-n-C₃H₇)C₂H₅ B-140C(═NOCH₃)C(═NO-i-C₃H₇)C₂H₅ B-141 C(═NOC₂H₅)C(═NOCH₃)C₂H₅ B-142C(═NOC₂H₅)C(═NOC₂H₅)C₂H₅ B-143 C(═NOC₂H₅)C(═NO-n-C₃H₇)C₂H₅ B-144C(═NOC₂H₅)C(═NO-i-C₃H₇)C₂H₅ B-145 CH═CH—CH₂CH₃ B-146 CH₂—CH═CH—CH₃ B-147CH₂—CH₂—CH═CH₂ B-148 C(CH₃)₂CH₂CH₃ B-149 CH═C(CH₃)₂ B-150 C(═CH₂)—CH₂CH₃B-151 C(CH₃)═CH—CH₃ B-152 CH(CH₃)CH═CH₂ B-153 CH═CH-n-C₃H₇ B-154CH₂—CH═CH—C₂H₅ B-155 (CH₂)₂—CH═CH—CH₃ B-156 (CH₂)₃—CH═CH₂ B-157CH═CH—CH(CH₃)₂ B-158 CH₂—CH═C(CH₃)₂ B-159 (CH₂)₂—C(CH₃)═CH₂ B-160CH═C(CH₃)—C₂H₅ B-161 CH₂—C(═CH₂)—C₂H₅ B-162 CH₂—C(CH₃)═CH—CH₃ B-163CH₂—CH(CH₃)—CH═CH₂ B-164 C(═CH₂)—CH₂—CH₂—CH₃ B-165 C(CH₃)═CH—CH₂—CH₃B-166 CH(CH₃)—CH═CH—CH₃ B-167 CH(CH₃)—CH₂—CH═CH₂ B-168 C(═CH₂)CH(CH₃)₂B-169 C(CH₃)═C(CH₃)₂ B-170 CH(CH₃)—C(═CH₂)—CH₃ B-171 C(CH₃)₂—CH═CH₂B-172 C(C₂H₅)═CH—CH₃ B-173 CH(C₂H₅)—CH═CH₂ B-174 CH═CH—CH₂—CH₂—CH₂—CH₃B-175 CH₂—CH═CH—CH₂—CH₂—CH₃ B-176 CH₂—CH₂—CH═CH—CH₂—CH₃ B-177CH₂—CH₂—CH₂—CH═CH—CH₃ B-178 CH₂—CH₂—CH₂—CH₂—CH═CH₂ B-179CH═CH—CH₂—CH(CH₃)CH₃ B-180 CH₂—CH═CH—CH(CH₃)CH₃ B-181CH₂—CH₂—CH═C(CH₃)CH₃ B-182 CH₂—CH₂—CH₂—C(CH₃)═CH₂ B-183CH═CH—CH(CH₃)—CH₂—CH₃ B-184 CH₂—CH═C(CH₃)—CH₂—CH₃ B-185CH₂—CH₂—C(═CH₂)—CH₂—CH₃ B-186 CH₂—CH₂—C(CH₃)═CH—CH₃ B-187CH₂—CH₂—CH(CH₃)—CH═CH₂ B-188 CH═C(CH₃)—CH₂—CH₂—CH₃ B-189CH₂—C(═CH₂)—CH₂—CH₂—CH₃ B-190 CH₂—C(CH₃)═CH—CH₂—CH₃ B-191CH₂—CH(CH₃)—CH═CH—CH₃ B-192 CH₂—CH(CH₃)—CH₂—CH═CH₂ B-193C(═CH₂)—CH₂—CH₂—CH₂—CH₃ B-194 C(CH₃)═CH—CH₂—CH₂—CH₃ B-195CH(CH₃)—CH═CH—CH₂—CH₃ B-196 CH(CH₃)—CH₂—CH═CH—CH₃ B-197CH(CH₃)—CH₂—CH₂—CH═CH₂ B-198 CH═CH—C(CH₃)₃ B-199 CH═C(CH₃)—CH(CH₃)—CH₃B-200 CH₂—C(═CH₂)—CH(CH₃)—CH₃ B-201 CH₂—C(CH₃)═C(CH₃)—CH₃ B-202CH₂—CH(CH₃)—C(═CH₂)—CH₃ B-203 C(═CH₂)—CH₂—CH(CH₃)—CH₃ B-204C(CH₃)═CH—CH(CH₃)—CH₃ B-205 CH(CH₃)—CH═C(CH₃)—CH₃ B-206CH(CH₃)—CH₂—C(═CH₂)—CH₃ B-207 CH═C(CH₂—CH₃)—CH₂—CH₃ B-208CH₂—C(═CH—CH₃)—CH₂—CH₃ B-209 CH₂—CH(CH═CH₂)—CH₂—CH₃ B-210C(═CH—CH₃)—CH₂—CH₂—CH₃ B-211 CH(CH═CH₂)—CH₂—CH₂—CH₃ B-212C(CH₂—CH₃)═CH—CH₂—CH₃ B-213 CH(CH₂—CH₃)—CH═CH—CH₃ B-214CH(CH₂—CH₃)—CH₂—CH═CH₂ B-215 CH₂—C(CH₃)₂—CH═CH₂ B-216C(═CH₂)—CH(CH₃)—CH₂—CH₃ B-217 C(CH₃)═C(CH₃)—CH₂—CH₃ B-218CH(CH₃)—C(═CH₂)—CH₂—CH₃ B-219 CH(CH₃)—C(CH₃)═CH—CH₃ B-220CH(CH₃)—CH(CH₃)—CH═CH₂ B-221 C(CH₃)₂—CH═CH—CH₃ B-222 C(CH₃)₂—CH₂—CH═CH₂B-223 C(═CH₂)—C(CH₃)₃ B-224 C(═CH—CH₃)—CH(CH₃)—CH₃ B-225CH(CH═CH₂)—CH(CH₃)—CH₃ B-226 C(CH₂—CH₃)═C(CH₃)—CH₃ B-227CH(CH₂—CH₃)—C(═CH₂)—CH₃ B-228 C(CH₃)₂—C(═CH₂)—CH₃ B-229C(CH₃)(CH═CH₂)—CH₂—CH₃ B-230 C(CH₃)(CH₂CH₃)—CH₂—CH₂—CH₃ B-231CH(CH₂CH₃)—CH(CH₃)—CH₂—CH₃ B-232 CH(CH₂CH₃)—CH₂—CH(CH₃)—CH₃ B-233C(CH₃)₂—C(CH₃)₃ B-234 C(CH₂—CH₃)—C(CH₃)₃ B-235 C(CH₃)(CH₂—CH₃)—CH(CH₃)₂B-236 CH(CH(CH₃)₂)—CH(CH₃)₂ B-237 CH═CH—CH₂—CH₂—CH₂—CH₂—CH₃ B-238CH₂—CH═CH—CH₂—CH₂—CH₂—CH₃ B-239 CH₂—CH₂—CH═CH—CH₂—CH₂—CH₃ B-240CH₂—CH₂—CH₂—CH═CH—CH₂—CH₃ B-241 CH₂—CH₂—CH₂—CH₂—CH═CH—CH₃ B-242CH₂—CH₂—CH₂—CH₂—CH₂—CH═CH₂ B-243 CH═CH—CH₂—CH₂—CH(CH₃)—CH₃ B-244CH₂—CH═CH—CH₂—CH(CH₃)—CH₃ B-245 CH₂—CH₂—CH═CH—CH(CH₃)—CH₃ B-246CH₂—CH₂—CH₂—CH═C(CH₃)—CH₃ B-247 CH₂—CH₂—CH₂—CH₂—C(═CH₂)—CH₃ B-248CH═CH—CH₂—CH(CH₃)—CH₂—CH₃ B-249 CH₂—CH═CH—CH(CH₃)—CH₂—CH₃ B-250CH₂—CH₂—CH═C(CH₃)—CH₂—CH₃ B-251 CH₂—CH₂—CH₂—C(═CH₂)—CH₂—CH₃ B-252CH₂—CH₂—CH₂—C(CH₃)═CH—CH₃ B-253 CH₂—CH₂—CH₂—CH(CH₃)—CH═CH₂ B-254CH═CH—CH(CH₃)—CH₂—CH₂—CH₃ B-255 CH₂—CH═C(CH₃)—CH₂—CH₂—CH₃ B-256CH₂—CH₂—C(═CH₂)—CH₂—CH₂—CH₃ B-257 CH₂—CH₂—C(CH₃)═CH—CH₂—CH₃ B-258CH₂—CH₂—CH(CH₃)—CH═CH—CH₃ B-259 CH₂—CH₂—CH(CH₃)—CH₂—CH═CH₂ B-260CH═C(CH₃)—CH₂—CH₂—CH₂—CH₃ B-261 CH₂—C(═CH₂)—CH₂—CH₂—CH₂—CH₃ B-262CH₂—C(CH₃)═CH—CH₂—CH₂—CH₃ B-263 CH₂—CH(CH₃)—CH═CH—CH₂—CH₃ B-264CH₂—CH(CH₃)—CH₂—CH═CH—CH₃ B-265 CH₂—CH(CH₃)—CH₂—CH₂—CH═CH₂ B-266C(═CH₂)—CH₂—CH₂—CH₂—CH₂—CH₃ B-267 C(CH₃)═CH—CH₂—CH₂—CH₂—CH₃ B-268CH(CH₃)—CH═CH—CH₂—CH₂—CH₃ B-269 CH(CH₃)—CH₂—CH═CH—CH₂—CH₃ B-270CH(CH₃)—CH₂—CH₂—CH═CH—CH₃ B-271 CH(CH₃)—CH₂—CH₂—CH₂—CH═CH₂ B-272CH═CH—CH₂—C(CH₃)₃ B-273 CH₂—CH═CH—C(CH₃)₃ B-274 CH═CH—CH(CH₃)—CH(CH₃)₂B-275 CH₂—CH═C(CH₃)—CH(CH₃)₂ B-276 CH₂—CH₂—C(═CH₂)—CH(CH₃)₂ B-277CH₂—CH₂—C(CH₃)═C(CH₃)₂ B-278 CH₂—CH₂—CH(CH₃)—C(═CH₂)—CH₃ B-279CH═C(CH₃)—CH₂—CH(CH₃)₂ B-280 CH₂—C(═CH₂)—CH₂—CH(CH₃)₂ B-281CH₂—C(CH₃)═CH—CH(CH₃)₂ B-282 CH₂—CH(CH₃)—CH═C(CH₃)₂ B-283CH₂—CH(CH₃)—CH₂—C(═CH₂)—CH₃ B-284 C(═CH₂)—CH₂—CH₂—CH(CH₃)₂ B-285C(CH₃)═CH—CH₂—CH(CH₃)₂ B-286 CH(CH₃)—CH═CH—CH(CH₃)₂ B-287CH(CH₃)—CH₂—CH═C(CH₃)₂ B-288 CH(CH₃)—CH₂—CH₂—C(═CH₂)—CH₃ B-289CH═CH—C(CH₃)₂—CH₂—CH₃ B-290 CH₂—CH₂—C(CH₃)₂—CH═CH₂ B-291CH═C(CH₃)—CH(CH₃)—CH₂—CH₃ B-292 CH₂—C(═CH₂)—CH(CH₃)—CH₂—CH₃ B-293CH₂—C(CH₃)═C(CH₃)—CH₂—CH₃ B-294 CH₂—CH(CH₃)—C(═CH₂)—CH₂—CH₃ B-295CH₂—CH(CH₃)—C(CH₃)═CH—CH₃ B-296 CH₂—CH(CH₃)—CH(CH₃)—CH═CH₂ B-297C(═CH₂)—CH₂—CH(CH₃)—CH₂—CH₃ B-298 C(CH₃)═CH—CH(CH₃)—CH₂—CH₃ B-299CH(CH₃)—CH═C(CH₃)—CH₂—CH₃ B-300 CH(CH₃)—CH₂—C(═CH₂)—CH₂—CH₃ B-301CH(CH₃)—CH₂—C(CH₃)═CH—CH₃ B-302 CH(CH₃)—CH₂—CH(CH₃)—CH═CH₂ B-303CH₂—C(CH₃)₂—CH═CH—CH₃ B-304 CH₂—C(CH₃)₂—CH₂—CH═CH₂ B-305C(═CH₂)—CH(CH₃)—CH₂—CH₂—CH₃ B-306 C(CH₃)═C(CH₃)—CH₂—CH₂—CH₃ B-307CH(CH₃)—C(═CH₂)—CH₂—CH₂—CH₃ B-308 CH(CH₃)—C(CH₃)═CH—CH₂—CH₃ B-309CH(CH₃)—CH(CH₃)—CH═CH—CH₃ B-310 CH(CH₃)—CH(CH₃)—CH₂—CH═CH₂ B-311C(CH₃)₂—CH═CH—CH₂—CH₃ B-312 C(CH₃)₂—CH₂—CH═CH—CH₃ B-313C(CH₃)₂—CH₂—CH₂—CH═CH₂ B-314 CH═CH—CH(CH₂—CH₃)—CH₂—CH₃ B-315CH₂—CH═C(CH₂—CH₃)—CH₂—CH₃ B-316 CH₂—CH₂—C(═CH—CH₃)—CH₂—CH₃ B-317CH₂—CH₂—CH(CH═CH₂)—CH₂—CH₃ B-318 CH═C(CH₂—CH₃)—CH₂—CH₂—CH₃ B-319CH₂—C(═CH—CH₃)—CH₂—CH₂—CH₃ B-320 CH₂—CH(CH═CH₂)—CH₂—CH₂—CH₃ B-321CH₂—C(CH₂—CH₃)═CH—CH₂—CH₃ B-322 CH₂—CH(CH₂—CH₃)—CH═CH—CH₃ B-323CH₂—CH(CH₂—CH₃)—CH—CH═CH₂ B-324 C(═CH—CH₃)—CH₂—CH₂—CH₂—CH₃ B-325CH(CH═CH₂)—CH₂—CH₂—CH₂—CH₃ B-326 C(CH₂—CH₃)═CH—CH₂—CH₂—CH₃ B-327CH(CH₂—CH₃)—CH═CH—CH₂—CH₃ B-328 CH(CH₂—CH₃)—CH₂—CH═CH—CH₃ B-329CH(CH₂—CH₃)—CH₂—CH₂—CH═CH₂ B-330 C(═CH—CH₂—CH₃)—CH₂—CH₂—CH₃ B-331C(CH═CH—CH₃)—CH₂—CH₂—CH₃ B-332 C(CH₂—CH═CH₂)—CH₂—CH₂—CH₃ B-333CH═C(CH₃)—C(CH₃)₃ B-334 CH₂—C(═CH₂)—C(CH₃)₃ B-335CH₂—C(CH₃)₂—CH(═CH₂)—CH₃ B-336 C(═CH₂)—CH(CH₃)—CH(CH₃)—CH₃ B-337C(CH₃)═C(CH₃)—CH(CH₃)—CH₃ B-338 CH(CH₃)—C(═CH₂)—CH(CH₃)—CH₃ B-339CH(CH₃)—C(CH₃)═C(CH₃)—CH₃ B-340 CH(CH₃)—CH(CH₃)—C(═CH₂)—CH₃ B-341C(CH₃)₂—CH═C(CH₃)—CH₃ B-342 C(CH₃)₂—CH₂—C(═CH₂)—CH₃ B-343C(CH₃)₂—C(═CH₂)—CH₂—CH₃ B-344 C(CH₃)₂—C(CH₃)═CH—CH₃ B-345C(CH₃)₂—CH(CH₃)CH═CH₂ B-346 CH(CH₂—CH₃)—CH₂—CH(CH₃)—CH₃ B-347CH(CH₂—CH₃)—CH(CH₃)—CH₂—CH₃ B-348 C(CH₃)(CH₂—CH₃)—CH₂—CH₂—CH₃ B-349CH(i-C₃H₇)—CH₂—CH₂—CH₃ B-350 CH═C(CH₂—CH₃)—CH(CH₃)—CH₃ B-351CH₂—C(═CH—CH₃)—CH(CH₃)—CH₃ B-352 CH₂—CH(CH═CH₂)—CH(CH₃)—CH₃ B-353CH₂—C(CH₂—CH₃)═C(CH₃)—CH₃ B-354 CH₂—CH(CH₂—CH₃)—C(═CH₂)—CH₃ B-355CH₂—C(CH₃)(CH═CH₂)—CH₂—CH₃ B-356 C(═CH₂)—CH(CH₂—CH₃)—CH₂—CH₃ B-357C(CH₃)═C(CH₂—CH₃)—CH₂—CH₃ B-358 CH(CH₃)—C(═CH—CH₃)—CH₂—CH₃ B-359CH(CH₃)—CH(CH═CH₂)—CH₂—CH₃ B-360 CH═C(CH₂—CH₃)—CH(CH₃)—CH₃ B-361CH₂—C(═CH—CH₃)—CH(CH₃)—CH₃ B-362 CH₂—CH(CH═CH₂)—CH(CH₃)—CH₃ B-363CH₂—C(CH₂—CH₃)═C(CH₃)—CH₃ B-364 CH₂—CH(CH₂—CH₃)—C(═CH₂)—CH₃ B-365C(═CH—CH₃)—CH₂—CH(CH₃)—CH₃ B-366 CH(CH═CH₂)—CH₂—CH(CH₃)—CH₃ B-367C(CH₂—CH₃)═CH—CH(CH₃)—CH₃ B-368 CH(CH₂—CH₃)CH═C(CH₃)—CH₃ B-369CH(CH₂—CH₃)CH₂—C(═CH₂)—CH₃ B-370 C(═CH—CH₃)CH(CH₃)—CH₂—CH₃ B-371CH(CH═CH₂)CH(CH₃)—CH₂—CH₃ B-372 C(CH₂—CH₃)═C(CH₃)—CH₂—CH₃ B-373CH(CH₂—CH₃)—C(═CH₂)—CH₂—CH₃ B-374 CH(CH₂—CH₃)—C(CH₃)═CH—CH₃ B-375CH(CH₂—CH₃)—CH(CH₃)—CH═CH₂ B-376 C(CH₃)(CH═CH₂)—CH₂—CH₂—CH₃ B-377C(CH₃)(CH₂—CH₃)—CH═CH—CH₃ B-378 C(CH₃)(CH₂—CH₃)—CH₂—CH═CH₂ B-379C[═C(CH₃)—CH₃]—CH₂—CH₂—CH₃ B-380 CH[C(═CH₂)—CH₃]—CH₂—CH₂—CH₃ B-381C(i-C₃H₇)═CH—CH₂—CH₃ B-382 CH(i-C₃H₇)—CH═CH—CH₃ B-383CH(i-C₃H₇)—CH₂—CH═CH₂ B-384 C(═CH—CH₃)—C(CH₃)₃ B-385 CH(CH═CH₂)—C(CH₃)₃B-386 C(CH₃)(CH═CH₂)CH(CH₃)—CH₃ B-387 C(CH₃)(CH₂—CH₃)C(═CH₂)—CH₃ B-3882-CH₃-cyclohex-1-enyl B-389 [2-(═CH₂)]-c-C₆H₉ B-3902-CH₃-cyclohex-2-enyl B-391 2-CH₃-cyclohex-3-enyl B-3922-CH₃-cyclohex-4-enyl B-393 2-CH₃-cyclohex-5-enyl B-3942-CH₃-cyclohex-6-enyl B-395 3-CH₃-cyclohex-1-enyl B-3963-CH₃-cyclohex-2-enyl B-397 [3-(═CH₂)]-c-C₆H₉ B-3983-CH₃-cyclohex-3-enyl B-399 3-CH₃-cyclohex-4-enyl B-4003-CH₃-cyclohex-5-enyl B-401 3-CH₃-cyclohex-6-enyl B-4024-CH₃-cyclohex-1-enyl B-403 4-CH₃-cyclohex-2-enyl B-4044-CH₃-cyclohex-3-enyl B-405 [4-(═CH₂)]-c-C₆H₉

The compounds of the formula I according to the invention can beprepared analogously to prior-art methods known per se, by the synthesesshown in the schemes below:

In scheme 1, n, R^(a), R¹, R² and A₁ to A₅ are as defined above. Informula II, A₁′ is N, NH or C—R^(3a). In formula II, for A₅=N, thevariable A₁′ is attached to A₂ and A₃ to A₄, and for A₅=C, the variableA₅ is attached to A₁′ and A₃ to A₄ or alternatively A₄ to A₅ and A₃ toA₂, in each case via a double bond. R is C₁-C₄-alkyl, in particularmethyl or ethyl.

According to scheme 1, in a first step, a hetarylamine of the formula IIis condensed with a suitably substituted dialkyl 2-phenylmalonate III.Examples of suitable hetarylamines of the formula II are 2-aminopyrrole,1-aminopyrazole, 1-amino-1,2,4-triazole, 1-amino-1,3,4-triazole,5-amino-1,2,3-triazole, 4-aminothiazole, 5-aminothiazole,4-aminoisothiazole, 5-aminoisothiazole, 4-aminothia-2,3-diazole,5-aminothia-2,3-diazole, 5-amino-1,2,3,4-tetrazole,1-alkyl-5-aminoimidazole, 1-alkyl-4-aminoimidazole and 2-aminoimidazole.Thus, when using:

1-aminopyrazole, the compounds I.a where R¹═R²═OH are obtained,

1-amino-1,2,4-triazole, the compounds I.b where R¹ ═R²═OH are obtained,

1-amino-1,3,4-triazole, the compounds I.c where R¹═R²═OH are obtained,

2-aminopyrrole, the compounds I.e where R¹═R²═OH are obtained,

5-aminoimidazole, the compounds I.f where R¹═R²═OH are obtained,

4-amino-1,2,3-triazole, the compounds I.h where R¹═R²═OH are obtained,

5-amino-1,2,3,4-tetrazole, the compounds I.k where R¹ ═R²═OH areobtained,

5-aminoisothiazole, the compounds I.m where R¹═R²═OH are obtained,

5-aminothiazole, the compounds I.n where R¹ ═R²═OH are obtained,

5-aminothia-2,3-diazole, the compounds I.o where R¹═R²═OH are obtained,

4-aminoisothiazole, the compounds I.p where R¹═R²═OH is obtained,

4-aminothiazole, the compounds I.q where R¹═R²═OH is obtained,

4-aminothia-2,3-diazole, the compounds I.r where R¹ ═R²═OH is obtained,

2-aminothiophene, the compounds I.s where R¹═R²═OH is obtained,

3-aminothiophene, the compounds I.t where R¹═R²═OH is obtained,

1-alkyl-5-aminoimidazole, the compounds I.u where R¹═R²═OH is obtained,

1-alkyl-4-aminoimidazole, the compounds I.v where R¹═R²═OH is obtained.

The condensation is generally carried out in the presence of a Brönstedtor Lewis acid as acidic catalyst or in the presence of a basic catalyst.Examples of suitable acidic catalysts are zinc chloride, phosphoricacid, hydrochloric acid, acetic acid, and mixtures of hydrochloric acidand zinc chloride. Examples of basic catalysts are tertiary amines, suchas triethylamine, tri-n-butylamine, pyridine bases, such as pyridine andquinoline, and amidine bases, such as DBN or DBU.

Condensation reactions of this type with acid catalysis are known inprinciple from the literature, for example from G. Saint-Ruf et al., J.Heterocycl. Chem. 1981, 18, pp. 1565-1570; I. Adachi et al., Chem. andPharm. Bull. 1987, 35, pp. 3235-3252; B. M Lynch et al., Can. J. Chem.1988, 66, pp. 420-428; Y. Blache et al., Heterocycles, 1994, 38, pp.1527-1532; V. D. Piaz et al., Heterocycles 1985, 23, pp. 2639-2644; A.Elbannany et al., Pharmazie 1988, 43, pp. 128-129; D. Brugier et al.,Tetrahedron 2000, pp. 56, 2985-2933; K. C. Joshi et al., J. Heterocycl.Chem. 1979, 16, pp. 1141-1145. The methods described in theseapplications can be used in an analogous manner for preparing thecompounds I according to the invention {R¹ ═R²═OH}.

The condensation reactions of this type with basic catalysis are knownin principle from the literature, for example from EP-A 770615. Themethod given in this application can be used in an analogous manner forpreparing the compounds I according to the invention {R¹═R²═OH}.

The condensation shown in scheme 1 gives azolo compounds of the formulaI in which R¹ and R² are both OH. Such azolo compounds I {R¹═R²═OH} areof particular interest as intermediates for preparing other azolocompounds I. The OH groups in these compounds can be converted in one ormore steps into other functional groups. In general, to this end, the OHgroups will initially be converted into halogen atoms, in particularinto chlorine atoms (see Scheme 1a).

This conversion can be achieved, for example, by reacting I {R¹ ═R²═OH)with a suitable halogenating agent (in Scheme 1a shown for achlorinating agent [Cl]). Suitable halogenating agents are, for example,phosphorus tribromide, phosphorus oxytribromide and in particularchlorinating agents such as POCl₃, PCl₃/Cl₂ and PCl₅, and mixtures ofthese reagents. The reaction can be carried out in excess halogenatingagent (POCl₃) or in an inert solvent, such as, for example, acetonitrileor 1,2-dichloroethane. For the chlorination, preference is given toreacting I {R¹═R²═OH} in POCl₃.

This reaction is usually carried out at from 10 to 180° C. For practicalreasons, the reaction temperature usually corresponds to the boilingpoint of the chlorinating agent (POCl₃) used or of the solvent. Theprocess is advantageously carried out with addition ofN,N-dimethylformamide or of nitrogen bases, such as, for example,N,N-dimethylaniline, in catalytic or stoichiometric amounts.

Analogously to the prior art quoted at the outset, the resulting dihalocompounds 1, for example the dichloro compounds I {R¹═R²═Cl} can then beconverted into other compounds I. Accordingly, azolo compounds of theformula I in which both R¹ and R² are halogen are of particular interestas intermediates for the preparation of other azolo compounds I. Suchconversions are summarized in Schemes 1b and 1c.

Thus, as shown in Scheme 1b, the dichloro compounds I {R¹═R²═Cl) can,for example, be reacted with an amine HNR⁷R⁸, giving a compound I inwhich R¹ is NR⁷R⁸ and R² is chlorine.

The method shown in the first step of Scheme 1 b is known in principlefrom WO 98/46607 and U.S. Pat. No. 5,593,996 for preparing5-chloro-7-amino-6-aryl-1,2,4]triazolo[1,5-a]pyrimidines and can beemployed in an analogous manner for preparing compounds I (R¹ ═NR⁷R⁸,R²═Cl}.

The reaction of the dichloro compounds I {R¹ ═R²=Cl} with an amineHNR⁷R⁸ is usually carried out at 0-150° C., preferably at 10-120° C., inan inert solvent, if appropriate in the presence of an auxiliary base.This method is known in principle, for example from J. Chem. Res. S (7),pp. 286-287 (1995) and Liebigs Ann. Chem., pp. 1703-1705 (1995), andfrom the prior art quoted at the outset, and can be employed in ananalogous manner for preparing the compounds according to the invention.

Suitable solvents are protic solvents, such as alcohols, for exampleethanol, and also aprotic solvents, for example aromatic hydrocarbons,halogenated hydrocarbons and ethers, for example toluene, o-, m- andp-xylene, diethyl ether, diisopropyl ether, tert-butyl methyl ether,dioxane, tetrahydrofuran, dichloromethane, in particular tert-butylmethyl ether and tetrahydrofuran, and also mixtures of the solventsmentioned above. Suitable auxiliary bases are, for example, thosementioned below: alkali metal carbonates and bicarbonates, such asNaHCO₃, and Na₂CO₃, alkali metal hydrogenphosphates, such as Na₂HPO₄,alkali metal borates, such as Na₂B₄O₇, tertiary amines and pyridinecompounds, diethylaniline and ethyldiisopropylamine. A suitableauxiliary base is also an excess of amine HNR⁷R⁸.

The components are usually employed in an approximately stoichiometricratio. However, it may be advantageous to use an excess of amine HNR⁷R⁸.

The amines HNR⁷R⁸ are commercially available or known from theliterature or can be prepared by known methods.

In the compound I obtained in this manner {R¹═NR⁷R⁸, R²=Cl}, thechlorine atom can be converted in a manner known per se into othersubstituents R².

Compounds of the formula I in which R² is OR⁶ are obtained from thecorresponding chloro compounds of the formula I {R¹ ═NR⁷R⁸, R²═Cl} byreaction with alkali metal hydroxides {OR⁶═OH}, alkali metal or alkalineearth metal alkoxides {OR⁶═O-alkyl, O-haloalkyl} [cf.: Heterocycles,Vol. 32, pp. 1327-1340 (1991); J. Heterocycl. Chem. Vol. 19, pp.1565-1567 (1982); Geterotsikl. Soedin, pp. 400-402 (1991)].Esterification of compounds where R²═OH by methods known per se affordscompounds I in which R² is O—C(O)R⁹. Compounds where R²═OH can beconverted by etherification methods known per se into the correspondingcompounds I in which R² is O-alkyl, O-haloalkyl or O-alkenyl.

Compounds of the formula I in which R² is cyano can be obtained from thecorresponding chloro compounds of the formula I {R¹ ═NR⁷R⁸, R²═Cl} byreaction with alkali metal, alkaline earth metal or transition metalcyanides, such as NaCN, KCN or Zn(CN)₂ [cf.: Heterocycles, Vol. 39, pp.345-356 (1994); Collect. Czech. Chem. Commun. Vol. 60, pp. 1386-1389(1995); Acta Chim. Scand., Vol. 50, pp. 58-63 (1996)].

The conversion of chloro compounds of the formula I {R¹═NR⁷R⁸, R²═Cl}into compounds of the formula I in which R² is C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,C₃-C₈-cycloalkyl, C₅-C₈-cycloalkenyl can be carried out in a mannerknown per se by reaction with organometallic compounds R^(2a)-Met inwhich R^(2a) is C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl; C₃-C₈-cycloalkyl, C₅-C₈-cycloalkenyl, and Met is lithium,magnesium or zinc. The reaction is preferably carried out in thepresence of catalytic or in particular at least equimolar amounts oftransition metal salts and/or transition metal compounds, in particularin the presence of Cu salts such as Cu(I)-halides and especiallyCu(I)-iodide. In general, the reaction is carried out in an inertorganic solvent, for example one of the ethers mentioned above, inparticular tetrahydrofuran, an aliphatic or cycloaliphatic hydrocarbon,such as hexane, cyclohexane and the like, an aromatic hydrocarbon, suchas toluene, or in a mixture of these solvents. The temperatures requiredfor this reaction are in the range of from −100 to +100° C. andespecially in the range of from −80° C. to +40° C.

Compounds of the formula I in which R¹ is NR⁷R⁸ and R² is methyl canalso be prepared from the chloro compounds of the formula I {R¹═NR⁷R⁸,R²═Cl} by reaction with a dialkyl malonate in the presence of a base orwith the alkali metal salt of a dialkyl malonate, followed by acidichydrolysis. The process is known in principle from U.S. Pat. No.5,994,360 and can be applied analogously to the preparation of compoundsI in which R¹ is NR⁷R⁸ and R² is methyl.

By appropriate modification of the synthesis shown in Scheme 1 b, it isalso possible to introduce in a first step instead of the group NR⁷R⁸ anitrile group, a group OR^(6′) {R^(6′)=alkyl} or a group S—R^(6″){R^(6″)═H or alkyl} as substituent R¹ using the methods described.

Compounds of the formula I in which R¹ is C₁-C₁₀-alkyl, where one carbonatom of the C₁-C₁₀-alkyl radical may be replaced by a silicium atom,C₁-C₆-haloalkyl, C₂-C₁₀-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,unsubstituted or substituted C₃-C₈-cycloalkyl, unsubstituted orsubstituted C₃-C₈-cycloalkyl-C₁-C₄-alkyl, unsubstituted or substitutedC₅-C₈-Cycloalkenyl can be prepared by the method shown in Scheme 1c byreacting the dichloro compound I {R¹═R²═Cl} in the manner describedabove with organometallic compounds R^(2a)-Met in which R^(2a) is asdefined above for R¹ and Met is lithium, magnesium or zinc.

The reaction shown in step a) can be carried out analogously to themethod described in WO 99/41255. In the resulting compounds, thechlorine atom (substituent R²) can be converted into other substituentsR² using the methods given for Scheme 1b.

Compounds of the formula I in which R¹ is C₁-C₁₀-alkyl, where one carbonatom of the C₁-C₁₀-alkyl radical may be replaced by a silicium atom,C₁-C₆-haloalkyl, C₂-C₁₀-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,unsubstituted or substituted C₃-C₈-cycloalkyl, unsubstituted orsubstituted C₃-C₈-cycloalkyl-C₁-C₄-alkyl, unsubstituted or substitutedC₅-C₈-cycloalkenyl can also be prepared analogously to the synthesisdescribed in Scheme 1, step a), by appropriate modification of thestarting materials of the formula III. These processes are shown inSchemes 1d and 1e.

According to Scheme 1 d, instead of the phenylmalonate of the formulaIII the starting material employed is a phenyl-β-ketoester of theformula IIIa in which R¹ is as defined above and R is C₁-C₄-alkyl, inparticular methyl or ethyl.

In the resulting compounds I, the hydroxyl group (substituent R²) canthen be converted into other substituents R² using the methods given forSchemes 1a, 1b and 1c.

According to Scheme 1e, 2-phenyl-β-diketones of the formula IIIb areemployed instead of the phenylmalonate of the formula III. Here, R¹ andR² independently of one another have the following meanings:C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,C₂-C₆-alkynyl, C₃-C₈-cycloalkyl or C₅-C₈-cycloalkenyl.

The phenylmalonates of the formula III used for preparing the compoundsI are known from the prior art cited at the outset or can be prepared ina manner known per se by Pd-catalyzed coupling of 2-bromomalonates withappropriately substituted phenylboronic acids or phenylboronic acidderivatives in a Suzuki coupling (for a review see A. Suzuki et al. inChem. Rev. 1995, 95, pp. 2457-2483). In an analogous manner, it is alsopossible to prepare substituted 2-phenyl-3-oxocarboxylic esters IIIa andsubstituted α-phenyl-β-diketones IIIb. α-Phenyl-β-diketones IIIb arefurthermore known from WO 02/74753.

Some of the hetarylamines of the formula II are commercially availableor known from the literature, for example from J. Het. Chem. 1970, 7, p.1159; J. Org. Chem. 1985, 50, p. 5520; Synthesis 1989, 4, p. 269;Tetrahedron Lett. 1995, 36, p. 9261, or they can be prepared in a mannerknown per se by reducing the corresponding nitro heteroaromaticcompounds.

A further route to the compounds of the formula I according to theinvention is shown in Scheme 2. Here, analogously to the method shown inScheme 1, step a), or to the method shown in Scheme 1e, a2-bromo-1,3-diketone of the formula IV is reacted with a hetarylamine ofthe formula II.

In Scheme 2, n, R^(a) and A₁ to A₅ are as defined above. In the formulaII, A₁′ is N, NH or CH. In formula II, for A₅═N, the variable A₁′ isattached to A₂ and A₃ to A₄, and for A₅═C, the variable A₅ is attachedto A₁′ and A₃ is attached to A₄ or alternatively A₄ is attached to A₅and A₃ is attached to A₂, in each case via a double bond. Independentlyof one another, R^(1a) and R^(2a) in the formula IV are: C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl orC₅-C₈-cycloalkenyl. In formula VI, (RO)₂B is a radical derived fromboric acid, for example (HO)₂B, (C₁-C₄-alkyl-O)₂B, or a radical derivedfrom boric anhydride. [Pd] is a palladium(0) complex which preferablyhas 4 trialkylphosphine or triarylphosphine ligands.

The reaction of II with IV is usually carried out under the basiccondensation conditions given for Scheme 1. Condensation reactions ofthis type with basic catalysis are known in principle from theliterature, for example from EP-A 770615. The method given in thispublication can be used in an analogous manner for preparing thecompounds V. The reaction of II with IV can also be carried out in thepresence of a Brönstedt or Lewis acid as acidic catalyst. Examples ofsuitable acidic catalysts are the acidic catalysts mentioned inconnection with Scheme 1, step a). The methods described there can beused in an analogous manner for preparing the compounds V according tothe invention (see also the literature cited there).

The compounds V obtained in the condensation are then reacted with aphenylboronic acid compound VI under the conditions of a Suzuki reaction(see above). The reaction t) conditions required for this are known fromthe literature, for example from A. Suzuki et al. in Chem. Rev. 1995,95, pp. 2457-2483 and J. Org. Chem. 1984, 49, p. 5237 and J. Org. Chem.2001, 66(21) pp. 7124-7128.

Compounds of the formula I.g in which R¹ and R² independently of oneanother are halogen, NR⁷R⁸, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl, C₅-C₈-cycloalkenylcan also be prepared according to the synthesis shown in Scheme 3:

In Scheme 3, n and R^(a) are as defined above. R is C₁-C₄-alkyl orC₁-C₄-haloalkyl, in particular methyl, and R¹ and R² independently ofone another are halogen, NR⁷R⁸, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl orC₅-C₈-cycloalkenyl. Preferably, R¹ in Scheme 3 is NR⁷R⁸ where R⁷, R⁸ areas defined above. R² is preferably halogen and in particular chlorine.

In step a) of Scheme 3, the pyrimidine compound VII is reacted in amanner known per se with hydrazine or hydrazine hydrate, giving thecompound of the formula VIII. Such reactions are known in principle fromthe literature, for example from D. T Hurst et al., Heterocycles 1977,6, pp. 1999-2004, and they can be employed in an analogous manner forpreparing the compounds VIII.

In step b), the 2-hydrazinopyrimidine IX is then cyclized with acarboxylic acid R^(3a)-COOH, in particular with formic acid or a formicacid equivalent, for example an orthoformate, such as triethylorthoformate, bis(dimethylamino)methoxymethane,dimethylamino(bismethoxy)methane and the like. The cyclization can becarried out in one step, as described in Heterocycles 1986, 24, pp.1899-1909; J. Chem. Res. 1995, 11, p. 434f.; J. Heterocycl. Chem. 1998,35, pp. 325-327; Pharmazie 2000, 55, pp. 356-358, J. Heterocycl.Chem.1990, 27, pp. 1559-1563; Org. Prep. Proced. Int. 1991, 23, pp.413-418; Liebigs Ann. Chem. 1984, pp. 1653-1661; Heterocycles, 1984, 22,p. 1821 or Chem. Ber. 1970,103, p. 1960. However, the reaction can alsobe carried out in two steps, by reacting, in a first step, the compoundVIII with triethyl orthoformate, bis(dimethylamino)methoxymethane ordimethylamino(bismethoxy)methane at elevated temperature in an aproticsolvent, for example an ether, such as tetrahydrofuran, ordimethylformamide, and then cyclizing the resulting intermediate withacid catalysis, giving the compound I. Methods for this purpose areknown, for example from Z. Chem. 1990, 20, 320f.; Croat. Chem. Acta1976, 48, pp. 161-167; Liebigs Ann. Chem. 1980, pp. 1448-1453; J. Chem.Soc. Perkin. Trans. 1984, pp. 993-998; J. Heterocycl. Chem. 1996, 33,pp. 1073-1077, and can be applied analogously to the preparation of thecompounds I.

Compounds of the formula VIIa are known in principle from WO 02/74753 orcan be prepared by the methods given in this application.

Compounds of the formula I.q in which R¹ is NR⁷R⁸ and R² is C₁-C₆-alkyl,C₁-C₆-haloalkyl or C₃-C₈-cycloalkyl can also be prepared according tothe synthesis shown in Scheme 4:

In Scheme 4, n, R^(a), R⁷ and R⁸ are as defined above. R^(2b) isC₁-C₄-alkyl, C₁-C₄-haloalkyl or C₃-C₈-cycloalkyl, in particular methyl.

In step a), a pyridine compound of the formula IX is brominated,preferably under acidic reaction conditions, for example in acetic acidby the method given in J. Org. Chem. 1983, 48, p. 1064. This gives a3,5-dibromopyridine of the formula X.

In a second step b), the 3,5-dibromopyridine X can be cyclized byreacting X with ethyl xanthogenate, for example KSC(S)OC₂H₅, to give6-mercaptothiazolo[4,5-b]pyridine of the formula XII, for example by themethod described in Synthetic Commun. 1996, 26, p. 3783. In step c),mercapothiazolo[4,5-b]pyridine XI is then reduced to givethiazolo[4,5-b]pyridine XII, for example with Raney-Nickel using themethod described by Metzger et al. in Bull. Soc. Chim. France, 1956, p.1701. Alternatively, the 3,5-dibromopyridine X can also be cyclizeddirectly to give thiazolo[4,5-b]pyridine XII (step b′), for example bythe method described by N. Suzuki in Chem. Pharm. Bull., 1979, 27(1),pp. 1-11.

The resulting thiazolo[4,5-b]pyridine XII is then reacted with aphenylboronic acid compound of the formula VI under the conditions of aSuzuki reaction by the method described in Scheme 2 (see above), whichgives the 3-(substituted)-phenylthiazolo[4,5-b]pyridine I.q.

The pyridine compound can be prepared by standard methods of organicchemistry, for example by the synthesis shown in Scheme 5

The compounds I are suitable as fungicides. They are distinguishedthrough an outstanding effectiveness against a broad spectrum ofphytopathogenic fungi, especially from the classes of the Ascomycetes,Deuteromycetes, Oomycetes and Basidiomycetes. Some are systemicallyeffective and they can be used in plant protection as foliar and soilfungicides.

They are particularly important in the control of a multitude of fungion various cultivated plants, such as wheat, rye, barley, oats, rice,maize, grass, bananas, cotton, soya, coffee, sugar cane, vines, fruitsand ornamental plants, and vegetables, such as cucumbers, beans,tomatoes, potatoes and cucurbits, and on the seeds of these plants.

They are especially suitable for controlling the following plantdiseases:

-   -   Alternaria species on fruit and vegetables,    -   Bipolaris and Drechslera species on cereals, rice and lawns,    -   Blumeria graminis (powdery mildew) on cereals,    -   Botrytis cinerea (gray mold) on strawberries, vegetables,        ornamental plants and grapevines,    -   Erysiphe cichoracearum and Sphaerotheca fuliginea on cucurbits,    -   Fusarium and Verticillium species on various plants,    -   Mycosphaerella species on cereals, bananas and peanuts,    -   Phytophthora infestans on potatoes and tomatoes,    -   Plasmopara viticola on grapevines,    -   Podosphaera leucotricha on apples,    -   Pseudocercosporella herpotrichoides on wheat and barley,    -   Pseudoperonospora species on hops and cucumbers,    -   Puccinia species on cereals,    -   Pyricularia oryzae on rice,    -   Rhizoctonia species on cotton, rice and lawns,    -   Septoria tritici and Stagonospora nodorum on wheat,    -   Uncinula necatoron grapevines,    -   Ustilago species on cereals and sugar cane, and    -   Venturia species (scab) on apples and pears.

The compounds I are also suitable for controlling harmful fungi, such asPaecilomyces variotii, in the protection of materials (e.g. wood, paper,paint dispersions, fibers or fabrics) and in the protection of storedproducts.

The compounds I are employed by treating the fungi or the plants, seeds,materials or soil to be protected from fungal attack with a fungicidallyeffective amount of the active compounds. The application can be carriedout both before and after the infection of the materials, plants orseeds by the fungi.

The fungicidal compositions generally comprise between 0.1 and 95%,preferably between 0.5 and 90%, by weight of active compound.

When employed in plant protection, the amounts applied are, depending onthe kind of effect desired, between 0.01 and 2.0 kg of active compoundper ha.

In seed treatment, amounts of active compound of 0.001 to 0.1 g,preferably 0.01 to 0.05 g, per kilogram of seed are generally necessary.

When used in the protection of materials or stored products, the amountof active compound applied depends on the kind of application area andon the desired effect. Amounts customarily applied in the protection ofmaterials are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg,of active compound per cubic meter of treated material.

The compounds I can be converted to the usual formulations, e.g.solutions, emulsions, suspensions, dusts, powders, pastes and granules.The application form depends on the respective intended use; it shouldin any case guarantee a fine and uniform distribution of the compoundaccording to the invention.

The formulations are prepared in a known way, e.g. by extending theactive compound with solvents and/or carriers, if desired usingemulsifiers and dispersants, it being possible, when water is thediluent, also to use other organic solvents as auxiliary solvents.Suitable auxiliaries for this purpose are essentially: solvents, such asaromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes),paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol),ketones (e.g. cyclohexanone), amines (e.g. ethanolamine,dimethylformamide) and water; carriers, such as ground natural minerals(e.g. kaolins, clays, talc, chalk) and ground synthetic ores (e.g.highly dispersed silicic acid, silicates); emulsifiers, such as nonionicand anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers,alkylsulfonates and arylsulfonates) and dispersants, such aslignosulfite waste liquors and methylcellulose.

Suitable surfactants are alkali metal, alkaline earth metal and ammoniumsalts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonicacid and dibutyinaphthalenesulfonic acid, alkylarylsulfonates, alkylsulfates, alkylsulfonates, fatty alcohol sulfates and fatty acids, andalkali metal and alkaline earth metal salts thereof, salts of sulfatedfatty alcohol glycol ether, condensation products of sulfonatednaphthalene and naphthalene derivatives with formaldehyde, condensationproducts of naphthalene or of naphthalenesulfonic acid with phenol andformaldehyde, polyoxyethylene octylphenol ethers, ethoxylatedisooctylphenol, octylphenol and nonylphenol, alkylphenol polyglycolethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols,isotridecyl alcohol, fatty alcohol ethylene oxide condensates,ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylatedpolyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitolesters, lignosulfite waste liquors and methylcellulose.

Petroleum fractions having medium to high boiling points, such askerosene or diesel fuel, furthermore coal tar oils, and oils ofvegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons,e.g. benzene, toluene, xylene, paraffin, tetrahydronaphthalene,alkylated naphthalenes or derivatives thereof, methanol, ethanol,propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol,cyclohexanone, chlorobenzene or isophorone, or highly polar solvents,e.g. dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone orwater, are suitable for the preparation of directly sprayable solutions,emulsions, pastes or oil dispersions.

Powders, preparations for broadcasting and dusts can be prepared bymixing or grinding together the active substances with a solid carrier.

Granules, e.g. coated granules, impregnated granules and homogeneousgranules, D can be prepared by binding the active compounds to solidcarriers. Solid carriers are, e.g., mineral earths, such as silica gels,silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess,clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate,magnesium oxide, ground synthetic materials, fertilizers, such as, e.g.,ammonium sulfate, ammonium phosphate, ammonium nitrate or ureas, andplant products, such as cereal meal, tree bark meal, wood meal andnutshell meal, cellulose powders and other solid carriers.

The formulations generally comprise between 0.01 and 95% by weight,preferably between 0.1 and 90% by weight, of the active compound. Theactive compounds are employed therein in a purity of 90% to 100%,preferably 95% to 100% (according to the NMR spectrum).

Examples of Formulations are:

-   I. 5 parts by weight of a compound according to the invention are    intimately mixed with 95 parts by weight of finely divided kaolin.    In this way, a dust comprising 5% by weight of the active compound    is obtained.-   II. 30 parts by weight of a compound according to the invention are    intimately mixed with a mixture of 92 parts by weight of pulverulent    silica gel and 8 parts by weight of liquid paraffin, which had been    sprayed onto the surface of this silica gel. In this way, an active    compound preparation with good adhesive properties (active compound    content 23% by weight) is obtained.-   III. 10 parts by weight of a compound according to the invention are    dissolved in a mixture consisting of 90 parts by weight of xylene, 6    parts by weight of the addition product of 8 to 10 mol of ethylene    oxide with 1 mol of the N-monoethanolamide of oleic acid, 2 parts by    weight of the calcium salt of dodecylbenzenesulfonic acid and 2    parts by weight of the addition product of 40 mol of ethylene oxide    with 1 mol of castor oil (active compound content 9% by weight).-   IV. 20 parts by weight of a compound according to the invention are    dissolved in a mixture consisting of 60 parts by weight of    cyclohexanone, 30 parts by weight of isobutanol, 5 parts by weight    of the addition product of 7 mol of ethylene oxide with 1 mol of    isooctylphenol and 5 parts by weight of the addition product of 40    mol of ethylene oxide with 1 mol of castor oil (active compound    content 16% by weight).-   V. 80 parts by weight of a compound according to the invention are    thoroughly mixed with 3 parts by weight of the sodium salt of    diisobutylnaphthalene-α-sulfonic acid, 10 parts by weight of the    sodium salt of a lignosulfonic acid from a sulfite waste liquor and    7 parts by weight of pulverulent silica gel and are ground in a    hammer mill (active compound content 80% by weight).-   VI. 90 parts by weight of a compound according to the invention are    mixed with 10 parts by weight of N-methyl-α-pyrrolidone and a    solution is obtained which is suitable for use in the form of very    small drops (active compound content 90% by weight).-   VII. 20 parts by weight of a compound according to the invention are    dissolved in a mixture consisting of 40 parts by weight of    cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight    of the addition product of 7 mol of ethylene oxide with 1 mol of    isooctylphenol and 10 parts by weight of the addition product of 40    mol of ethylene oxide with 1 mol of castor oil. By running the    solution into 100 000 parts by weight of water and finely dispersing    it therein, an aqueous dispersion is obtained comprising 0.02% by    weight of the active compound.-   VIII. 20 parts by weight of a compound according to the invention    are thoroughly mixed with 3 parts by weight of the sodium salt of    diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of the    sodium salt of a lignosulfonic acid from a sulfite waste liquor and    60 parts by weight of pulverulent silica gel and are ground in a    hammer mill. A spray emulsion comprising 0.1% by weight of the    active compound is obtained by fine dispersion of the mixture in 20    000 parts by weight of water.

The active compounds can be used as such, in the form of theirformulations or of the application forms prepared therefrom, e.g. in theform of directly sprayable solutions, powders, suspensions ordispersions, emulsions, oil dispersions, pastes, dusts, preparations forbroadcasting or granules, by spraying, atomizing, dusting, broadcastingor watering. The application forms depend entirely on the intended uses;they should always ensure the finest possible dispersion of the activecompounds according to the invention.

Aqueous application forms can be prepared from emulsifiableconcentrates, pastes or wettable powders (spray powders, oildispersions) by addition of water. To prepare emulsions, pastes or oildispersions, the substances can be homogenized in water, as such ordissolved in an oil or solvent, by means of wetting agents, tackifiers,dispersants or emulsifiers. However, it is also possible to prepareconcentrates comprising active substance, wetting agent, tackifier,dispersant or emulsifier and possibly solvent or oil which are suitablefor dilution with water.

The concentrations of active compound in the ready-for-use preparationscan be varied within relatively wide ranges. In general, they arebetween 0.0001 and 10%, preferably between 0.01 and 1%.

The active compounds can also be used with great success in theultra-low volume (ULV) process, it being possible to apply formulationswith more than 95% by weight of active compound or even the activecompound without additives.

Oils of various types, herbicides, fungicides, other pesticides andbactericides can be added to the active compounds, if need be also notuntil immediately before use (tank mix). These agents can be added tothe preparations according to the invention in a weight ratio of 1:10 to10:1.

The preparations according to the invention can, in the application formas fungicides, also be present together with other active compounds,e.g. with herbicides, insecticides, growth regulators, fungicides oralso with fertilizers. On mixing the compounds I or the preparationscomprising them in the application form as fungicides with otherfungicides, in many cases an expansion of the fungicidal spectrum ofactivity is obtained.

The following list of fungicides, with which the compounds according tothe invention can be conjointly used, is intended to illustrate thepossible combinations:

-   -   acylalanines, such as benalaxyl, metalaxyl, ofurace or oxadixyl,    -   amine derivatives, such as aldimorph, dodine, dodemorph,        fenpropimorph, fenpropidin, guazatine, iminoctadine, spiroxamine        or tridemorph,    -   anilinopyrimidines, such as pyrimethanil, mepanipyrim or        cyprodinyl,    -   antibiotics, such as cycloheximide, griseofulvin, kasugamycin,        natamycin, polyoxin or streptomycin,    -   azoles, such as bitertanol, bromoconazole, cyproconazole,        difenoconazole, dinitroconazole, epoxiconazole, fenbuconazole,        fluquinconazole, flusilazole, hexaconazole, imazalil,        metconazole, myclobutanil, penconazole, propiconazole,        prochloraz, prothioconazole, tebuconazole, triadimefon,        triadimenol, triflumizole or triticonazole,    -   dicarboximides, such as iprodione, myclozolin, procymidone or        vinclozolin,    -   dithiocarbamates, such as ferbam, nabam, maneb, mancozeb, metam,        metiram, propineb, polycarbamate, thiram, ziram or zineb,    -   heterocyclic compounds, such as anilazine, benomyl, boscalid,        carbendazim, carboxin, oxycarboxin, cyazofamid, dazomet,        dithianon, famoxadone, fenamidone, fenarimol, fuberidazole,        flutolanil, furametpyr, isoprothiolane, mepronil, nuarimol,        probenazole, proquinazid, pyrifenox, pyroquilon, quinoxyfen,        silthiofam, thiabendazole, thifluzamide, thiophanate-methyl,        tiadinil, tricyclazole or triforine,    -   copper fungicides, such as Bordeaux mixture, copper acetate,        copper oxychloride or basic copper sulfate,    -   nitrophenyl derivatives, such as binapacryl, dinocap, dinobuton        or nitrophthal-isopropyl,    -   phenylpyrroles, such as fenpiclonil or fludioxonil,    -   sulfur,    -   other fungicides, such as acibenzolar-S-methyl, benthiavalicarb,        carpropamid, chlorothalonil, cyflufenamid, cymoxanil, dazomet,        diclomezine, diclocymet, diethofencarb, edifenphos, ethaboxam,        fenhexamid, fentin acetate, fenoxanil, ferimzone, fluazinam,        fosetyl, fosetyl-aluminum, iprovalicarb, hexachlorobenzene,        metrafenone, pencycuron, propamocarb, phthalide,        tolciofos-methyl, quintozene or zoxamide,    -   strobilurins, such as azoxystrobin, dimoxystrobin,        fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin,        picoxystrobin, pyraclostrobin or trifloxystrobin,    -   sulfenic acid derivatives, such as captafol, captan,        dichlofluanid, folpet or tolylfluanid,    -   cinnamides and analogous compounds, such as dimethomorph,        flumetover or flumorph.

SYNTHESIS EXAMPLES

The procedures described in the following synthesis examples were usedto prepare further compounds I by appropriate modification of thestarting compounds. The compounds thus obtained are listed in thefollowing tables, together with physical data.

Example 1 7-Phenyl-8-isobutyl-6-methyl-[1,2,4]triazolo[4,3-b]pyridazine1.1 7-Bromo-8-isobutyl-6-methyl-[1,2,4]triazolo[4,3-b]pyridazine

At 0° C., a solution of 32 g (0.2 mol) of bromine in 100 ml of carbontetrachloride was added dropwise to a solution of 28.6 g (0.2 mol) of6-methylheptane-2,4-dione in 120 ml of carbon tetrachloride and 120 mlof water. After the addition had ended, the reaction mixture was stirredat 0° C. for 45 minutes. The organic phase was separated off and driedover anhydrous magnesium sulfate, the drying agent was filtered off andthe mixture was, under reduced pressure, concentrated to dryness, whichgave 44 g of the brominated dione. The crude intermediate obtained wasdissolved in 400 ml of glacial acetic acid, 16.8 g (0.2 mol) of1,2,4-triazol-4-ylamine were added and the reaction mixture was heatedat reflux for 1.5 hours. The organic solvent was removed and tert-butylmethyl ether, water and 1 N aqueous sodium hydroxide solution wereadded. After phase separation, the organic phase was dried, the dryingagent was filtered off and the mixture was, under reduced pressure,concentrated to dryness, which gave a dark oil. The resulting oil waspurified by silica gel chromatography (mobile phase: cyclohexane+ethylacetate (2:1 v/v), which gave 6.6 g of7-bromo-8-isobutyl-6-methyl-[1,2,4]triazolo[4,3-b]pyridazine as aviscous oil.

¹H-NMR (CDCl₃) δ [ppm]: 1.0 (d, 6H), 2.5 (m, 1H), 2.7 (s, 3H), 3.2 (d,2H), 9.0 (s, 1H).

1.2 7-Phenyl-8-isobutyl-6-methyl-[1,2,4]triazolo[4,3-b]pyridazine

A mixture of 0.5 mmol of7-bromo-8-isobutyl-6-methyl-[1,2,4]triazolo[4,3-b]pyridazine fromExample 5.1, 0.75 mmol of phenylboronic acid, 1.5 mmol of sodiumbicarbonate and 0.03 mmol of tetrakis(triphenylphosphine)palladium(0) in5 ml of tetrahydrofuran and 2 ml of water was heated at reflux for 24hours. The reaction mixture was then allowed to cool to room temperatureand filtered through Celite. Under reduced pressure, the filtrate wasconcentrated to dryness, and the residue obtained was purified by silicagel column chromatography (mobile phase: cyclohexane+ethyl acetate),which gave 0.08 g of the title compound.

¹H-NMR (CDCl₃) δ [ppm]: 0.8 (d, 2H), 2.2 (s, 3H), 2.4 (m, 1H), 2.7 (d,2H), 7.2 (d, 2H), 7.5 (m, 3H), 9.0 (s, 1H).

The compounds of the formula I.c {R^(3a)═H} listed in Table 1a belowwere prepared in an analogous manner: TABLE 1a (I.c)

¹H-NMR (CDCl₃) [δ] or melting Ex. # R¹ C₆H_(5-n)(R^(a))_(n) point [° C.]2 2-methylpropyl 2-methyl-4- 9.05(s), 7.10(m), 2.95(dd), fluorophenyl2.45(m), 2.20(s), 2.05(s), 1.90(d), 1.75(d) 3 n-butyl 2-methyl-4-9.05(s), 7.10(m), 2.85(m), fluorophenyl 2.55(m), 2.20(s), 2.10(s),1.75(m), 1.35(m), 1.80(t) 4 n-butyl 2,4- 9.05(s), 7.20(m), 7.05(m),2.85(f), difluorophenyl 1.70(m), 1.30(m), 1.80(f) 5 n-butyl 2-fluoro-4-9.00(s), 7.15(m), 2.85(m), 2.50(s), methylphenyl 2.30(s), 1.70(m),1.30(m), 1.80(f) 6 2-methylpropyl 2,4- 92° C. difluorophenyl 72-methylpropyl 2-fluoro-4- 9.05(s), 7.10(m), 2.75(m), 2.50(f),methylphenyl 2.30(s), 1.65(d), 1.60(d) 8 cyclohexyl 2,4- 1.11 (m, 2H);1.42 (m, 2H); 1.62 difluorophenyl (m, 2H), 1.78 (m, 2H); 2.20 (s, 3H);2.50 (m, 3H); 7.03 (m, 2H); 7.11 (m, 1H); 9.00 (s, 1H); 9 cyclohexyl2,4-dimethyl- 1.10 (m, 2H); 1.33 (m, 2H); 1.50 phenyl (m, 2H); 1.67 (m,2H); 2.03 (s, 3H); 2.10 (s, 3H); 2.32 (m, 1H); 2.40 (s, 3H); 2.45 (m,1H); 2.64 (m, 1H); 6.90 (d, 1H); 7.12 (a, 1H); 7.18 (s, 1H); 9.00 (s,1H); 10 cyclohexyl 2-methyl-4- 1.10 (m, 2H); 1.43 (m, 2H); 1.62fluorophenyl (m, 2H), 1.80 (t, 2H); 2.08 (s, 3H); 2.13 (s, 3H); 2.40 (m,2H); 2.67 (m, 1H); 7.05 (m, 3H); 9.03 (s, 1H); 11 CH₂CH₂C(CH₃)₃2,4-difluoro- 0.80 (s, 9H); 1.53 (dd, 2H); 2.28 phenyl (s, 3H); 2.78(dd, 2H); 7.05 (m, 2H); 7.20 (m, 1H); 9.04 (s, 1H); 12 CH₂CH₂C(CH₃)₃2-fluoro-4- 0.80 (s, 9H); 1.43 (ddd, 1H); 1.62 methylphenyl (ddd, 1H);2.08 (s, 3H); 2.18 (s, 3H); 2.50 (ddd, 1H); 2.86 (ddd, 1H); 7.07 (m,3H); 9.03 (s, 1H); 13 CH(CH₃)(CH₂CH₂CH₃) 2-methyl-4- 0.78 (q, 3H); 1.06(m, 1H); 1.23 fluorophenyl (m, 1H); 1.45 (dd, 3H); 1.90 (m, 1H); 2.09(d, 3H); 2.13 (d, 3H); 2.65 (m, 1H); 7.05 (m, 3H); 7.18 (s, 1H); 9.03(s, 1H); 14 CH(CH₃)(CH₂CH₂CH₃) 2,4-dimethyl- 0.79 (m, 3H); 1.05 (m, 1H);1.23 phenyl (m, 1H); 1.43 (dd, 3H); 1.87 (m, 1H); 2.07 (d, 3H); 2.13 (d,3H); 2.19 (m, 1H); 2.40 (s, 3H); 2.70 (m, 1H); 6.92 (d, 1H); 7.13 (d,1H); 7.18 (s, 1H); 9.02 (s, 1H); 15 CH₂CH₂C(CH₃)₃ 2,4-dimethyl- 0.78 (s,9H); 1.45 (ddd, 1H); 1.62 phenyl (ddd, 1H); 2.03 (s, 3H); 2.17 (s, 3H);2.40 (s, 3H); 2.52 (ddd, 1H); 2.85 (ddd, 1H); 6.95 (d, 1H); 7.13 (d,1H); 7.18 (s, 1H); 9.02 (s, 1H); 16 CH(CH₃)CH(CH₃)CH₂CH₃ 2-methyl-4-0.68 (m, 3H); 0.91 (d, 3H); 1.13 fluorophenyl (m, 1H); 1.46 (d, 3H);1.70 (m, 1H); 2.08 (s, 3H); 2.12 (d, 3H); 2.34 (m, 1H); 2.59 (m, 1H);7.04 (m, 3H); 9.02 (s, 1H); 17 CH(CH₃)CH(CH₃)CH₂CH₃ 2,4-difluoro- 0.69(m, 3H); 0.92 (m, 3H); 1.12 phenyl (m, 1H); 1.44 (m, 3H); 1.70 (m, 1H);2.22 (s, 3H); 2.38 (m, 1H); 2.68 (m, 1H); 7.03 (m, 2H); 7.17 (m, 1H);9.04 (s, 1H); 18 (CH(CH₃)(CH₂)₂CH₃ 2,4-difluoro- 0.75 (t, 3H); 1.09 (m,1H); 1.19 (1 diastereomer, R_(f): 0,5)* phenyl (m, 1H); 1.47 (d, 3H);1.83 (m, 1H); 2.22 (s, 3H); 2.28 (m, 1H); 2.76 (m, 1H); 7.04 (m, 2H);7.17 (m, 1H); 9.02 (s, 1H); 19 CH(CH₃)(CH₂)₂CH₃ 2-fluoro-4- 0.74 (t,3H); 1.09 (m, 1H); 1.19 (1 diastereomer; R_(f): 0,4)* methylphenyl (m,1H); 1.49 (d, 3H); 1.77 (m, 1H); 2.25 (s, 3H); 2.29 (m, 1H); 2.49 (s,3H); 2.80 (m, 1H); 7.06 (m, 3H); 9.02 (s, 1H); 20 (CH(CH₃)CH(CH₃)CH₂CH₃2-fluoro-4- 0.69 (m, 3H); 0.91 (m, 3H); 1.14 (1 diastereomer; R_(f):0,5)* methylphenyl (m, 1H); 1.43 (d, 3H); 1.78 (m, 1H); 2.22 (d, 3H);2.45 (m, 1H); 2.46 (s, 3H); 2.68 (m, 1H); 7.06 (m, 3H); 9.02 (s, 1H); 21CHCH₃(CH₂)₂CH₃ 2,4-difluoro- 0.75 (t, 3H); 1.09 (m, 2H); 1.50 (d, (1diastereomer; R_(f): 0,4)* phenyl 3H); 1.75 (m, 1H); 2.23 (s, 3H); 2.29(m, 1H); 2.75 (m, 1H); 7.03 (m, 2H); 7.14 (m, 1H); 9.02 (s, 1H); 22CH(CH₃)CH(CH₃)CH₂CH₃ 2-fluoro-4- 0.60 (m, 3H); 0.88 (d, 3H); 1.10 (1diastereomer; R_(f): 0,4)* methylphenyl (m, 1H); 1.46 (d, 3H); 1.72 (m,1H); 2.22 (s, 3H); 2.44 (s, 3H); 2.45 (m, 1H); 2.63 (m, 1H); 7.03 (m,3H); 9.02 (s, 1H);R_(f)value determined by thin-layer chromatography on silica gel(eluent:cyclohexane/ethyl acetate (1:5))

Example 235-Chloro-6-(2-chloro-6-fluorophenyl)-7-(4-methylpiperidin-1-yl)-tetrazolo[1,5-a]pyrimidine23.1.5,7-Dihydroxy-6-(2-chloro-6-fluorophenyl)tetrazolo[1,5-a]pyrimidine

A mixture of 5-aminotetrazole (0.15 mol), 2-aminotetrazole (0.15 mol),diethyl 2-(2-chloro-6-fluorophenyl)malonate (0.15 mol) and tributylamine(50 ml) was heated at 180° C. for 6 hours. The reaction mixture wascooled to 70° C., a solution of 21 g of sodium hydroxide in 22 ml ofwater was added and the mixture was stirred for 30 minutes. The organicphase was separated off and the aqueous phase was extracted with diethylether. The aqueous phase was acidified with concentrated hydrochloricacid. The precipitate was filtered off and dried, which gave 7 g of theproduct.

23.2. 5,7-Dichloro-6-(2-chloro-6-fluorophenyl)tetrazolo[1,5-a]pyrimidine

A mixture of5,7-dihydroxy-6-(2-chloro-6-fluorophenyl)tetrazolo[1,5-a]pyrimidine (6g) from Example 23.1. and phosphorus oxychloride (20 ml) was heated atreflux for 8 hours. Some of the phosphorus oxychloride was thendistilled off. The residue was poured into a mixture of dichloromethaneand water. The organic phase was separated off, dried with anhydroussodium sulfate and filtered. The filtrate was concentrated under reducedpressure, which gave 4 g of the title compound.

23.3.5-Chloro-6-(2-chloro-6-fluorophenyl)-7-(4-methylpiperidin-1-yl)-tetrazolo[1,5-a]pyrimidine

A mixture of 4-methylpiperidine (1.5 mmol), triethylamine (1.5 mmol) anddichloromethane (10 ml) was added with stirring to a mixture of5,7-dichloro-6-(2-chloro-6-fluorophenyl)tetrazolo[1,5-a]pyrimidine (1.5mmol, from QUA, Example 23.2) and dichloromethane (20 ml). The mixturewas stirred at room temperature for 16 hours and then washed with dilutehydrochloric acid (5%). The organic phase was separated off, dried withanhydrous sodium sulfate and filtered. The filtrate was concentratedunder reduced pressure and the residue was purified by silica gel columnchromatography, which gave 0.26 g of the product.

The compounds of the general formula I.k (R²═Cl,(R^(a))_(n)=2,4,6-trifluoromethyl) listed in Table 1b below wereprepared in analogous way: TABLE 1b (I.k)

¹H-NMR (CDCl₃) [δ] or melting Ex. # R¹ point [° C.] 24 isopropylamino142-146 25 NH((S) CH(CH₃)CH(CH₃)₂) 85-86 26 NH((S) CH(CH₃)C(CH₃)₃) 85-8627 sec-butylamino 116 28 4-methylpiperidin-1-yl 0.92 (d, 3H); 1.03 (m,2H); 1.58 (m, 2H); 1.58 (m, 1H); 2.76 (m, 2H); 3.95 (m, 2H); 6.80 (m,2H); 29 NH((R) CH(CH₃)CH(CH₃)₂) 0.86 (m, 6H); 1.08 (d, 3H); 1.74 (m,1H); 4.15 (m, 1H); 4.42 (d, 1H); 6.86 (m, 2H); 30 Cl 6.82 (m, 2H);

Example 317-Chloro-5-isopropylamino-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo-[4,3-a]pyrimidine31.1.6-Chloro-2-hydrazino-4-isopropylamino-5-(2,4,6-trifluorophenyl)pyrimidine

16.3 g (43 mmol) of6-chloro-4-isopropylamino-2-methylsulfonyl-5-(2,4,6-trifluoro-phenyl)pyrimidinewere suspended in 50 ml of ethanol, 5.3 g (0.17 mol) of hydrazinehydrate were added and the mixture was heated at reflux for 90 minutes.The reaction mixture was then concentrated under reduced pressure andthe residue was taken up in ethanol, dried over sodium sulfate andreconcentrated. The residue was then purified by silica gel columnchromatography (mobile phase: cyclohexane:ethyl acetate (2:1)). Thisgave 14.2 g of the product as a light-yellow solid. Melting point143-150° C.

31.2.N,N-Dimethyl-N′-(4-chloro-6-isopropylamino-5-(2,4,6-trifluorophenyl)pyrimidin-2-yl)hydrazonoformamide

6 ml of dimethoxymethyldimethylamine were added to a solution of 1.0 g(3 mmol) of the hydrazinopyrimidine from 31.1 in 10 ml oftetrahydrofuran and the mixture was stirred at room temperature for 16 hand under reflux for 2 h. The reaction mixture was concentrated underreduced pressure and the residue was then purified chromatographicallyon silica gel (mobile phase: cyclohexane:ethyl acetate (2:1)). This gave0.6 g of the product as a light-brown solid of melting point 204-207° C.

31.3.7-Chloro-5-isopropylamino-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[4,3-a]pyrimidine

0.25 g (0.65 mmol) of the pyrimidine compound from 31.2. was dissolvedin 12.5 ml of tetrahydrofuran. 0.2 g (3.3 mmol) of acetic acid was addedand the mixture was stirred at room temperature for 15 h and at 40° C.and 60° C. for 2 h and then concentrated under reduced pressure. Theresidue was purified chromatographically on silica gel (mobile phase:cyclohexane: methyl tert-butyl ether (2:1)). This gave 0.18 g of theproduct as a beige solid of melting point 268-273° C.

Example 332-Methyl-4-(4-methylpiperidin-1-yl)-3-(2,4,6-trifluorophenyl)-imidazo[1,5-a]pyrimidine-8-carbonitrile33.14-Hydroxy-2-methyl-3-(2,4,6-trifluorophenyl)-imidazo[1,5-a]pyrimidin-8-carboxamide

A mixture of 31.0 g (0.119 mol) of ethyl3-oxo-2-(2,4,6-trifluorophenyl)butyrate, 19.4 g (0.119 mol) of4-aminoimidazol-5-carboxamide-hydrochloride and 22.0 g (0.119 mol) oftributylamin were stirred for 15 h at 140° C. The suspension obtainedupon cooling the reaction mixture was diluted with methyl tert-butylether and ethyl acetate and the obtained solids were isolated. Thesolids were washed with methyl tert-butyl ether and ethyl acetate anddried in a vacuum-drying cabinet at 40° C. Thus, 31.2 g of a mixture ofthe regioisomers of the title compound were obtained.

33.24-Chloro-2-methyl-3-(2,4,6-trifluorophenyl)-imidazo[1,5-a]pyrimidine-8-carbonitrile

A mixture of 31.2 g (0.097 mol) of4-hydroxy-2-methyl-3-(2,4,6-trifluorophenyl)-imidazo[1,5-a]pyrimidine-8-carboxamidefrom example 33.1 and 180 ml (20 equivalents) of phosphorus oxychloridewas heated to reflux for 40 h with stirring. After cooling the reactionmixture was diluted with methyl tert-butyl ether and the mixture wasadded dropwise within 45 min. at 30° C. to a dilute solution of sodiumhydroxide. The obtained suspension was filtered over silica gel andwashed with methyl tert-butyl ether. The aqueous layer was extractedwith methyl tert-butyl ether and the combined organic layers were washedwith water, dried with sodium sulfate and concentrated. The residue waspurified by chromatography on silica gel (eluent: cyclohexane:ethylacetate). Thereby, 0.5 mg of the title compound having a melting pointof 183° C. and 2.4 g of the other regioisomer were obtained.

33.32-Methyl-4-(4-methylpiperidin-1-yl)-3-(2,4,6-trifluorophenyl)-imidazo[1,5-a]pyrimidine-8-carbonitrile

A mixture of 0.15 g (0.46 mmol) of4-chloro-2-methyl-3-(2,4,6-trifluorophenyl)-imidazo[1,5-a]pyrimidine-8-carbonitrilefrom example 33.2, 0.1 g (0.92 mmol) of methylpiperidine und 0.1 g (0.92mmol) of triethylamine in 2 ml of tetrahydrofuran were heated to refluxfor 72 h. After cooling methyl tert-butyl ether and 2N hydrochloric acidwere added. The aqueous phase of the thus obtained mixture was extractedwith methyl tert.-butyl ether and the combined organic layers werewashed with water and the organic layer was dried over sodium sulfateand concentrated. Chromatography on silicagel of the residue (eluent:cyclohexane/ethyl acetate) yielded 100 mg of2-methyl-4-(4-methylpiperidin-1-yl)-3-(2,4,6-trifluorophenyl)-imidazo[1,5-a]pyrimidine-8-carbonitrile.

Example 342-Methoxy-4-methyl-3-(2,4,6-trifluorophenyl)-imidazo[1,5-a]pyrimidin-8-carbonitril

0.2 g (0.62 mmol) of2-chloro-4-methyl-3-(2,4,6-trifluorphenyl)-imidazo[1,5-a]pyrimidine-8-carbonitrilefrom example 33.2 and 0.11 g (0.62 mmol) of 30% solution of sodiummethylate were stirred for 45 h at room temperature in 2 ml of methanol.Then, dichloromethane and 2N hydrochloric acid were added. The organiclayer was separated, dried over sodium sulfate and concentrated, therebyyielding 0,17 g of the title compound having a melting poing of 225° C.

Example 354-Methyl-2-methylamino-3-(2,4,6-trifluorophenyl)-imidazo[1,5-a]pyrimidin-8-carbonitrilr

A mixture of 0.2 g (0.62 mmol) of2-chloro-4-methyl-3-(2,4,6-trifluorophenyl)-imidazo[1,5-a]pyrimidin-8-carbonitrilefrom example 33.2, 0.1 g (1.24 mmol) of methylamine and 0.23 g (1.24mmol) of triethylamine in 2 ml of methanol were stirred at 35° C. for 24h. Then, dichloromethane and 2N hydrochloric acid were added. Theorganic layer was separated, dried over sodium sulfate and concentrated.Thus, 60 mg of the title compound were obtained.

The compounds of the formula I.f {(R^(a))_(n)=2,4,6-trifluoro) listed inTable 1c below were prepared analogously. Table 1c also containsspectroscopic data of the compounds of examples 33 to 37 and the meltingpoint of the compound of example 34: TABLE 1c (I.f)

¹H-NMR (CDCl₃) [δ] Ex. # R¹ R² or melting point [° C.] 32 CH₃ Cl 183 334-methylpiperidin-1-yl CH₃ 0.99 (d, 3H); 1.28 (m, 2H); 1.53 (m, 1H);1.72 (m, 2H); 2.32 (s, 3H); 2.62 (m, 2H); 3.24 (m, 2H); 6.89 (m, 2H);7.93 (m, 1H); 34 CH₃ OCH₃ 225 35 CH₃ methylamino 2.37 (s, 3H); 3.06 (d,3H); 4.67 (s, 1H); 6.93 (m, 2H); 7.72 (s, 1H); 36 NH((R)CH(CH₃)CH(CH₃)₂) CH₃ 0.82 (m, 6H); 1.08 (d, 3H); 1.71 (m, 1H); 2.25 (s,3H); 3.37 (m, 1H); 4.54 (d, 1H); 6.90 (m, 2H); 8.17 (s, 1H); 37sec-butylamino CH₃ 207-210

Example 387-(2,4-Difluorophenyl)-8-isobutyl-6-methyl-[1,2,4]triazolo[1,5-b]pyridazine

The title compound was prepared according to the method of example 1.

Melting point: 103-105° C.

Examples of the Activity Against Harmful Fungi

The fungicidal action of the compounds of the formula I was demonstratedby the following experiments:

For use examples 1 and 2, the active compounds were formulated as astock solution 15 with 0.25% by weight of active compound in acetone ordimethyl sulfoxide (DMSO). 1% by weight of the emulsifier Uniperol® EL(wetting agent having emulsifying and dispersant action based onethoxylated alkylphenols) was added to this solution, and the mixturewas diluted with water to the desired concentration.

Use Example 1 Activity Against Early Blight of Tomato Caused byAlternaria solani, Protective Use

Leaves of potted plants of the tomato cultivar “Large Fruited St.Pierre” were sprayed to runoff point with an aqueous suspension havingthe concentration of active compound stated below. The next day, theleaves were infected with an aqueous spore suspension of Alternariasolani in a 2% biomalt solution having a density of 0.17×10⁶ spores/ml.The plants were then placed in a water-vapor-saturated chamber at 20-22°C. After 5 days, the blight on the untreated but infected control plantshad developed to such an extent that the infection could be determinedvisually in %. TABLE 2 Active compound No. Infection [%] at 250 ppmExample 1 10 Example 2 15 Example 3 25 Example 4 10 Example 7 20 Example8 0 Example 11 20 Example 12 3 Example 13 10 Example 16 20 Example 36 7Untreated 80

Use Example 2 Activity against Peronospora of Grapevines caused byPlasmopara viticola, Protective Use

Leaves of potted grapevines of the cultivar “Müller-Thurgau” weresprayed to runoff point with an aqueous suspension having theconcentration of active compound stated below. The next day, theundersides of the leaves were inoculated with an aqueous zoosporesuspension of Plasmopara viticola. The grapevines were then initiallyplaced in a water-vapor-saturated chamber at 24° C. for 48 hours andthen in a greenhouse at 20-30° C. for 5 days. After this period of time,the plants were again placed in a humid chamber for 16 hours to promotesporangiophore eruption. The extent of the development of the infectionon the undersides of the leaves was then determined visually. TABLE 3Active compound No. Infection [%] at 250 ppm Example 1 20 Example 2 0Example 3 0 Example 4 0 Example 5 0 Example 6 0 Example 8 0 Example 9 20Example 10 0 Example 11 0 Example 12 3 Example 15 3 Example 18 10Example 21 3 Untreated 90

Use Example 3 Activity Against Mildew of Wheat Caused by Erysiphe [syn.Blumeria] graminis form a Specialis tritici, Protective Use

Leaves of wheat seedlings, grown in pots, of the cultivar “Newton” weresprayed to runoff point with an aqueous suspension having theconcentration of active compound stated below. The suspension oremulsion was prepared from a stock solution comprising 5% of activecompound, 94% of cyclohexanone and 1% of emulsifier (Tween 20) bydilution with water. 3-5 hours after the spray coating had dried on, thespores were dusted with mildew of wheat (Erysiphe [syn. Blumeria]graminis form a specialis. tritici). The test plants were then placed ina greenhouse at 20-24° C. and 60-90% relative atmospheric humidity.After 7 days, the extent of the mildew development was determinedvisually in % infection of the entire leaf area. TABLE 4 Active compoundNo. Infection [%] at 250 ppm Example 14 20 Example 15 20 Example 18 7Example 19 20 Example 20 5 Example 21 3 Example 22 7 Example 23 15Untreated 90

1-16. (canceled)
 17. A bicyclic compound of the formula I

in which A₁ or A₅ is C and the other of the two variables A₁, A₅ is N, Cor C—R³; A₂, A₃, A₄ independently of one another are N or C—R^(3a),where one of the variables A₂, A₃ or A₄ may also be S or a group N—R⁴ ifA₁ and A₅ are both C, and where A₄ is not N or C—R^(3a) if A₁ is N, A³is C—R^(3a) and A₅ is C, and where A₁ is attached to A₂ and A₃ to A₄ orA₂ is attached to A₃ and A₄ to A₅ or A₁ is attached to A₅ and A₂ to A₃or A₁ is attached to A₅ and A₃ to A₄ or A₁ is attached to A₂ and A₄ toA₅ by double bonds; n is 0, 1, 2,3, 4 or 5; R^(a) is halogen, cyano,C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy,C₂-C₆-alkenyl, C₂-C₆-alkenyloxy or C(O)R⁵; R¹ is halogen, cyano,C₁-C₁₀-alkyl, where a carbon atom of the C₁-C₁₀-alkyl radical may bereplaced by a silicium atom, C₁-C₆-haloalkyl, C₂-C₁₀-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl,C₃-C₈-cycloalkyl-C₁-C₄-alkyl, where the cycloalkyl moiety of the twolast-mentioned groups may be unsubstituted or contain 1, 2, 3, 4, 5, or6 radicals selected from the group consisting of C₁-C₄-alkylidene,C₁-C₄-alkyl, halogen, C₁-C₄-haloalkyl and hydroxy and the alkyl moietyof C₃-C₈-cycloalkyl-C₁-C₄-alkyl may be unsubstituted or contain 1, 2, 3,or 4 radicals selected from the group consisting of halogen,C₁-C₄-haloalkyl and hydroxy, C₅-C₈-cycloalkenyl which may beunsubstituted or contain 1, 2, 3 or 4 radicals selected from the groupconsisting of C₁-C₄-alkyl, halogen, C₁-C₄-haloalkyl and hydroxy, OR⁶,SR⁶, Nk⁷R⁸, a radical of the formula —C(R¹¹)(R¹²)C(═NOR¹³)(R¹⁴) or aradical of the formula —C(═NOR¹⁵)C(═NOR¹⁶)(R¹⁷); R² is halogen, cyano,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,C₂-C₆-alkynyl, C₃-C₈-cycloalkyl, C₅-C₈-cycloalkenyl, OR⁶ SR⁶ or NR⁷R⁸;R³, R^(3a) independently of one another are hydrogen, CN, halogen,C₁-C₆-alkyl or C₂-C₆-alkenyl; R⁴ is hydrogen, C₁-C₆-alkyl orC₂-C₆-alkenyl; R⁵ is hydrogen, OH, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, C₂-C₆-alkenyl, C₁-C₆-alkylamino ordi-C₁-C₆-alkylamino, piperidin-1-yl, pyrrolidin-1-yl or morpholin-4-yl;R⁶ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl or COR⁹; R⁷,R⁸ independently of one another are hydrogen, C₁-C₁₀-alkyl,C₂-C₁₀-alkenyl, C₄-C₁₀-alkadienyl, C₂-C₁₀-alkynyl, C₃-C₈-cycloalkyl,C₅-C₈-cycloalkenyl, C₅-C₁₀-bicycloalkyl, phenyl, naphthyl, a 5- or6-membered saturated or partially unsaturated heterocycle which may have1, 2 or 3 heteroatoms selected from the group consisting of N, O and Sas ring members or a 5- or 6-membered aromatic heterocycle which mayhave 1, 2 or 3 heteroatoms selected from the group consisting of N, Oand S as ring members, where the radicals mentioned as R⁷, R⁸ may bepartially or fully halogenated and/or may have 1, 2 or 3 radicals R^(b)where R^(b) is selected from the group consisting of cyano, nitro, OH,C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy,C₁-C₆-alkylthio, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkynyl,C₂-C₆-alkynyloxy, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, piperidin-1-yl,pyrrolidin-1-yl or morpholin-4-yl; R⁷ and R⁸ together with the nitrogenatom to which they are attached may also form a 5-, 6- or 7-memberedsaturated or unsaturated heterocycle which may have 1, 2, 3 or 4 furtherheteroatoms selected from the group consisting of O, S, N and NR¹⁰ asring members, which may be partially or fully halogenated and which mayhave 1, 2 or 3 radicals R^(b); R⁹, R¹⁰ independently of one another arehydrogen or C₁-C₆-alkyl; R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷ independentlyof one another are hydrogen or C₁₋C₆-alkyl; or an agriculturallyacceptable salt of the compound I, except for compounds of the formula Iin which R¹ and R² are both OH or both halogen if A₁ is Nand A₅ is C.18. A compound as claimed in claim 17 of the formula I in which R¹ ishalogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,C₂-C₆-alkinyl, C₃-C₈-cycloalkyl, C₅-C₈-cycloalkenyl, OR⁶, SR⁶ or NR⁷R⁸;and R² is halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,C₂-C₆-alkinyl, C₃-C₈-cycloalkyl, C₅-C₈-cycloalkenyl, OR⁶, SR⁶ or NR⁷R⁸.19. A compound as claimed in claim 17 of the formula I in which A₁ is Cand A₅ is N and A₂, A₃ and A₄ independently of one another are N orC—R^(3a).
 20. A compound as claimed in claim 19 of the formula I inwhich A₂ is N.
 21. A compound as claimed in claim 17 of the formula I inwhich A₁ and A₃ are N, A₅ is C and A₂ and A₄ independently of oneanother are N or C—R^(3a).
 22. A compound as claimed in claim 17 of theformula I in which A₁ is N and A₅ is C and A₂, A₃ and A₄ independentlyof one another are C—R^(3a).
 23. A compound as claimed in claim 17 ofthe formula I in which A₁ and A₅ are C, one of the variables A₂ or A₄ issulfur and the other of the variables A₂ or A₄ and the variable A₃independently of one another are C—R^(3a) or N.
 24. A compound asclaimed in claim 17, wherein in formula I A₁, A₂ A₃ and A₄ are N and A₅is C.
 25. A compound as claimed in claim 17, wherein in formula I A₁ andA₃ denote N, A₂ and A₄ each are C—R^(3a) and A₅ is C.
 26. A compound asclaimed in claim 17, wherein in formula I A₂ A₃ and A₅ denote N, A₁ is Cand A₄ is C—R^(3a).
 27. A compound as claimed in claim 17 of the formulaI in which n is 1, 2, 3 or
 4. 28. A compound as claimed in claim 17 ofthe formula I in which the group

where R^(a1) is fluorine, chlorine or methyl; R^(a2) is hydrogen orfluorine; R^(a3) is hydrogen, fluorine, chlorine, C₁-C₄-alkyl orC₁-C₄-alkoxy; R^(a4) is hydrogen or fluorine; R^(a5) is hydrogen,fluorine, chlorine or C₁-C₄-alkyl.
 29. A compound as claimed in claim 17of the formula I in which R¹ is a group NR⁷R⁸ where at least one of theradicals R⁷, R⁸ is different from hydrogen.
 30. A compound as claimed inclaim 29 of the formula I in which R⁷ is C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₂-C₆-alkynyl or C₂-C₆-alkenyl; R⁸ is hydrogen or C₁-C₆-alkyl; or R⁷, R⁸together with the nitrogen atom to which they are attached are asaturated or partially unsaturated nitrogen heterocycle which may haveone further heteroatom selected from the group consisting of O, S andNR¹⁰ as ring member and which may have 1 or 2 substituents selected fromthe group consisting of C₁-C₆-alkyl and C₁-C₆-haloalkyl, where R¹⁰ is asdefined in claim
 1. 31. A compound as claimed in claim 29 of the formulaI where R² is halogen or C₁-C₄-alkyl.
 32. A compound as claimed in claim17 of the formula I where R¹ is C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₃-C₈-cycloalkyl or C₃-C₈-cycloalkenyl and R² isC₁-C₄-alkyl.
 33. The use of a compound of the formula I as claimed inclaim 17 or of an agriculturally acceptable salt thereof for controllingphytopathogenic fungi.
 34. A composition for controlling phytopathogenicfungi, which composition comprises at least one compound of the formulaI as claimed in claim 17 and/or an agriculturally acceptable salt offormula I and at least one solid or liquid carrier.
 35. A method forcontrolling phytopathogenic fungi, which method comprises treating thefungi or the materials, plants, the soil or the seeds to be protectedagainst fungal attack with an effective amount of a compound of theformula I as claimed in claim 17 and/or with an agriculturallyacceptable salt of I.